1 - Science of Synthesis: Knowledge Updates 2012/2 [Seite 1]
1.1 - Title page [Seite 5]
1.2 - Imprint [Seite 7]
1.3 - Preface [Seite 8]
1.4 - Abstracts [Seite 10]
1.5 - Overview [Seite 18]
1.6 - Table of Contents [Seite 20]
1.7 - Volume 4: Compounds of Group 15 (As, Sb, Bi) and Silicon Compounds [Seite 42]
1.7.1 - 4.4 Product Class 4: Silicon Compounds [Seite 42]
1.7.1.1 - 4.4.25.11 Acylsilanes [Seite 42]
1.7.1.1.1 - 4.4.25.11.1 Synthesis of Acylsilanes [Seite 42]
1.7.1.1.1.1 - 4.4.25.11.1.1 Method 1: Synthesis of Simple Acylsilanes [Seite 42]
1.7.1.1.1.1.1 - 4.4.25.11.1.1.1 Variation 1: Hydrolysis of Acetals [Seite 42]
1.7.1.1.1.1.2 - 4.4.25.11.1.1.2 Variation 2: Oxidation of Organocuprates [Seite 44]
1.7.1.1.1.1.3 - 4.4.25.11.1.1.3 Variation 3: Nucleophilic Substitution of Morpholine Amides [Seite 48]
1.7.1.1.1.1.4 - 4.4.25.11.1.1.4 Variation 4: Additional Synthetic Methods [Seite 49]
1.7.1.1.1.2 - 4.4.25.11.1.2 Method 2: Synthesis of Bis(acylsilanes) [Seite 51]
1.7.1.1.1.3 - 4.4.25.11.1.3 Method 3: Synthesis of a-Oxo Acylsilanes [Seite 54]
1.7.1.1.1.4 - 4.4.25.11.1.4 Method 4: Synthesis of a,ß-Unsaturated Acylsilanes [Seite 56]
1.7.1.1.1.5 - 4.4.25.11.1.5 Method 5: Synthesis of a-Amino Acylsilanes [Seite 57]
1.7.1.1.2 - 4.4.25.11.2 Applications of Acylsilanes [Seite 59]
1.7.1.1.2.1 - 4.4.25.11.2.1 Method 1: Applications of Simple Acylsilanes [Seite 59]
1.7.1.1.2.1.1 - 4.4.25.11.2.1.1 Variation 1: Nucleophilic Addition [Seite 59]
1.7.1.1.2.1.2 - 4.4.25.11.2.1.2 Variation 2: Nucleophilic Addition with Brook Rearrangement [Seite 68]
1.7.1.1.2.1.3 - 4.4.25.11.2.1.3 Variation 3: Acylsilanes as Acyl Anion Precursors [Seite 81]
1.7.1.1.2.1.4 - 4.4.25.11.2.1.4 Variation 4: Enolate and Enol Ether Reactions [Seite 94]
1.7.1.1.2.1.5 - 4.4.25.11.2.1.5 Variation 5: Photochemistry [Seite 95]
1.7.1.1.2.1.6 - 4.4.25.11.2.1.6 Variation 6: Miscellaneous Applications [Seite 99]
1.7.1.1.2.2 - 4.4.25.11.2.2 Method 2: Applications of Bis(acylsilanes) [Seite 103]
1.7.1.1.2.3 - 4.4.25.11.2.3 Method 3: Applications of a-Oxo Acylsilanes [Seite 106]
1.7.1.1.2.4 - 4.4.25.11.2.4 Method 4: Applications of a,ß-Unsaturated Acylsilanes [Seite 117]
1.8 - Volume 8: Compounds of Group 1 (Li . Cs) [Seite 126]
1.8.1 - 8.1 Product Class 1: Lithium Compounds [Seite 126]
1.8.1.1 - 8.1.34 Asymmetric Lithiation [Seite 126]
1.8.1.1.1 - 8.1.34.1 Method 1: Deprotonation in a Position a to a Heteroatom [Seite 128]
1.8.1.1.1.1 - 8.1.34.1.1 Variation 1: Enantioselective Deprotonation of Carbamates and Their Analogues [Seite 128]
1.8.1.1.1.2 - 8.1.34.1.2 Variation 2: Enantioselective Deprotonation of Phosphorylated Derivatives [Seite 134]
1.8.1.1.1.3 - 8.1.34.1.3 Variation 3: Enantioselective Deprotonation of Ureas [Seite 138]
1.8.1.1.1.4 - 8.1.34.1.4 Variation 4: Enantioselective Deprotonation of Phosphoramidates [Seite 140]
1.8.1.1.1.5 - 8.1.34.1.5 Variation 5: Enantioselective Deprotonation Followed by Transmetalation [Seite 141]
1.8.1.1.1.6 - 8.1.34.1.6 Variation 6: Enantioselective Deprotonation Followed by Cyclization [Seite 147]
1.8.1.1.1.7 - 8.1.34.1.7 Variation 7: Enantioselective Deprotonation Followed by Wittig Rearrangement [Seite 150]
1.8.1.1.1.8 - 8.1.34.1.8 Variation 8: Diastereoselective Deprotonation of Carbamates [Seite 155]
1.8.1.1.1.9 - 8.1.34.1.9 Variation 9: Diastereoselective and Enantioselective Deprotonations of Epoxides or Aziridines [Seite 159]
1.8.1.1.1.10 - 8.1.34.1.10 Variation 10: Catalytic Enantioselective Deprotonation [Seite 161]
1.8.1.1.2 - 8.1.34.2 Method 2: Deprotonation in a Position Lacking an a-Heteroatom [Seite 166]
1.8.1.1.2.1 - 8.1.34.2.1 Variation 1: Diastereoselective Deprotonation in a Benzylic Position [Seite 166]
1.8.1.1.2.2 - 8.1.34.2.2 Variation 2: Enantioselective Deprotonation in a Benzylic Position [Seite 167]
1.8.1.1.2.3 - 8.1.34.2.3 Variation 3: Diastereoselective Deprotonation of Metallocene Derivatives [Seite 169]
1.8.1.1.2.4 - 8.1.34.2.4 Variation 4: Enantioselective Deprotonation of Metallocene Derivatives [Seite 171]
1.8.1.1.3 - 8.1.34.3 Method 3: Tin-Lithium Exchange [Seite 173]
1.8.1.1.4 - 8.1.34.4 Method 4: Reductive Lithiation [Seite 176]
1.8.1.1.5 - 8.1.34.5 Method 5: Carbometalation [Seite 177]
1.8.1.1.5.1 - 8.1.34.5.1 Variation 1: Enantioselective Intermolecular Carbolithiation [Seite 177]
1.8.1.1.5.2 - 8.1.34.5.2 Variation 2: Enantioselective and Diastereoselective Intramolecular Carbolithiation [Seite 180]
1.9 - Volume 13: Five-Membered Hetarenes with Three or More Heteroatoms [Seite 190]
1.9.1 - 13.32 Product Class 32: 1,2,3-Trithioles, Their Benzo Derivatives, and Selenium and Tellurium Analogues [Seite 190]
1.9.1.1 - 13.32.1 Product Subclass 1: 1,2,3-Trithioles [Seite 190]
1.9.1.1.1 - 13.32.1.1 Synthesis by Ring-Closure Reactions [Seite 191]
1.9.1.1.1.1 - 13.32.1.1.1 By Formation of Two S--S Bonds [Seite 191]
1.9.1.1.1.1.1 - 13.32.1.1.1.1 Method 1: Synthesis from Metal Enedithiolates with Thionyl Chloride [Seite 191]
1.9.1.1.1.2 - 13.32.1.1.2 By Formation of Two C--S Bonds [Seite 191]
1.9.1.1.1.2.1 - 13.32.1.1.2.1 Method 1: Synthesis from Alkynes with Sulfur [Seite 191]
1.9.1.1.2 - 13.32.1.2 Synthesis by Ring Transformation [Seite 192]
1.9.1.1.2.1 - 13.32.1.2.1 Method 1: Formal Germanium/Sulfur Exchange of a 1,3,2-Dithiagermole with Thionyl Chloride [Seite 192]
1.9.1.1.2.2 - 13.32.1.2.2 Method 2: Formal Ring Expansion with the Insertion of an Extra Sulfur Atom [Seite 193]
1.9.1.2 - 13.32.2 Product Subclass 2: 1,2,3-Benzotrithioles and Other Ring-Fused Analogues [Seite 194]
1.9.1.2.1 - 13.32.2.1 Synthesis by Ring-Closure Reactions [Seite 195]
1.9.1.2.1.1 - 13.32.2.1.1 By Formation of Two S--S Bonds and One C--C Bond [Seite 195]
1.9.1.2.1.1.1 - 13.32.2.1.1.1 Method 1: Electrochemical Reduction of Carbon Disulfide [Seite 195]
1.9.1.2.1.2 - 13.32.2.1.2 By Formation of Two S--S Bonds [Seite 196]
1.9.1.2.1.2.1 - 13.32.2.1.2.1 Method 1: Synthesis from Arene-1,2-dithiols [Seite 196]
1.9.1.2.1.2.1.1 - 13.32.2.1.2.1.1 Variation 1: Reactions with Sulfur Dichloride [Seite 196]
1.9.1.2.1.2.1.2 - 13.32.2.1.2.1.2 Variation 2: Reactions with Thionyl Chloride [Seite 196]
1.9.1.2.1.2.1.3 - 13.32.2.1.2.1.3 Variation 3: Reactions with Thionyl Chloride, Sodium Iodide, and Perchloric Acid [Seite 197]
1.9.1.2.1.2.2 - 13.32.2.1.2.2 Method 2: Synthesis from Metal Enedithiolates with Sulfur Dichloride [Seite 198]
1.9.1.2.1.2.2.1 - 13.32.2.1.2.2.1 Variation 1: Reactions with Lithium or Sodium Enedithiolates [Seite 198]
1.9.1.2.1.2.2.2 - 13.32.2.1.2.2.2 Variation 2: Reactions with Zinc Enedithiolates [Seite 199]
1.9.1.2.1.3 - 13.32.2.1.3 By Formation of Two C--S Bonds [Seite 200]
1.9.1.2.1.3.1 - 13.32.2.1.3.1 Method 1: Synthesis from 1,2-Dibromoarenes with Sulfur [Seite 200]
1.9.1.2.1.3.1.1 - 13.32.2.1.3.1.1 Variation 1: Reactions in Liquid Ammonia [Seite 200]
1.9.1.2.1.3.1.2 - 13.32.2.1.3.1.2 Variation 2: Reaction in Diazabicycloundecene [Seite 201]
1.9.1.2.2 - 13.32.2.2 Synthesis by Ring Transformation [Seite 201]
1.9.1.2.2.1 - 13.32.2.2.1 Method 1: Synthesis from 1,3,2-Dithiametalloles [Seite 201]
1.9.1.2.2.1.1 - 13.32.2.2.1.1 Variation 1: Reactions of 1,3,2-Benzodithiatitanoles with Sulfur Dichloride [Seite 202]
1.9.1.2.2.1.2 - 13.32.2.2.1.2 Variation 2: Reactions of 1,3,2-Benzodithiastannoles with Sulfur Dichloride [Seite 202]
1.9.1.2.2.1.3 - 13.32.2.2.1.3 Variation 3: Reactions of 1,3,2-Benzodithiastannoles with Thionyl Chloride [Seite 203]
1.9.1.2.2.1.4 - 13.32.2.2.1.4 Variation 4: Reactions of 1,3,2-Benzodithiastannoles with Thionyl Chloride, Sodium Iodide, and Perchloric Acid [Seite 204]
1.9.1.2.2.1.5 - 13.32.2.2.1.5 Variation 5: Reactions of 1,3,2-Benzodithiastannoles with Thionyl Chloride, Trimethylsilyl Trifluoromethanesulfonate, and Samarium(II) Iodide [Seite 206]
1.9.1.2.2.2 - 13.32.2.2.2 Method 2: Synthesis from 1,2,3-Benzochalcogenadiazoles with Sulfur [Seite 207]
1.9.1.2.2.2.1 - 13.32.2.2.2.1 Variation 1: Reactions of 1,2,3-Benzothiadiazoles [Seite 207]
1.9.1.2.2.2.2 - 13.32.2.2.2.2 Variation 2: Reactions with 1,2,3-Benzoselenadiazoles [Seite 207]
1.9.1.2.2.3 - 13.32.2.2.3 Method 3: Synthesis from 1,3-Benzodithiol-2-ones [Seite 208]
1.9.1.2.2.3.1 - 13.32.2.2.3.1 Variation 1: Reactions with Sodium Hydrogen Sulfide [Seite 208]
1.9.1.2.2.3.2 - 13.32.2.2.3.2 Variation 2: Reactions with an Alkyllithium and Sulfur Dichloride [Seite 209]
1.9.1.2.2.3.3 - 13.32.2.2.3.3 Variation 3: Reactions with a Sodium Alkoxide and Sulfur Dichloride [Seite 210]
1.9.1.2.2.4 - 13.32.2.2.4 Method 4: Synthesis from 1,3-Benzodithiole-2-thiones [Seite 210]
1.9.1.2.2.5 - 13.32.2.2.5 Method 5: Ring Contraction [Seite 211]
1.9.1.2.2.5.1 - 13.32.2.2.5.1 Variation 1: Synthesis from 1,3,5,2,4-Benzotrithiadiazepines by Thermolysis [Seite 211]
1.9.1.2.2.5.2 - 13.32.2.2.5.2 Variation 2: Synthesis from Benzopentathiepins [Seite 212]
1.9.1.2.3 - 13.32.2.3 Synthesis by Substituent Modification [Seite 213]
1.9.1.2.3.1 - 13.32.2.3.1 One-Electron Oxidation [Seite 213]
1.9.1.2.3.1.1 - 13.32.2.3.1.1 Method 1: Synthesis from 1,2,3-Benzotrithioles with Nitrosonium Hexafluorophosphate To Give Radical Cationic Salts [Seite 213]
1.9.1.2.3.2 - 13.32.2.3.2 Addition Reactions [Seite 214]
1.9.1.2.3.2.1 - 13.32.2.3.2.1 Method 1: Synthesis from 1,2,3-Benzotrithioles by Oxidation [Seite 214]
1.9.1.2.3.3 - 13.32.2.3.3 Rearrangement of Substituents [Seite 215]
1.9.1.2.3.3.1 - 13.32.2.3.3.1 Method 1: Synthesis from 1,2,3-Benzotrithiole 2-Oxides by Photochemical Rearrangement [Seite 215]
1.9.1.3 - 13.32.3 Product Subclass 3: 1,2,3-Benzodithiaselenoles [Seite 216]
1.9.1.3.1 - 13.32.3.1 Synthesis by Ring-Closure Reactions [Seite 217]
1.9.1.3.1.1 - 13.32.3.1.1 By Formation of One S--S and One S--Se Bond [Seite 217]
1.9.1.3.1.1.1 - 13.32.3.1.1.1 Method 1: Synthesis from 2-(Chlorosulfonyl)benzeneselenenyl Bromide and Thioacetamide [Seite 217]
1.9.1.3.2 - 13.32.3.2 Synthesis by Ring Transformation [Seite 217]
1.9.1.3.2.1 - 13.32.3.2.1 Method 1: Synthesis from 1,3,2-Benzothiaselenastannoles [Seite 217]
1.9.1.3.2.1.1 - 13.32.3.2.1.1 Variation 1: Reactions with Sulfur in Liquid Ammonia [Seite 217]
1.9.1.3.2.1.2 - 13.32.3.2.1.2 Variation 2: Reactions with Thionyl Chloride, Sodium Iodide, and Perchloric Acid [Seite 218]
1.9.1.4 - 13.32.4 Product Subclass 4: 1,3,2-Benzodithiaselenoles [Seite 219]
1.9.1.4.1 - 13.32.4.1 Synthesis by Ring-Closure Reactions [Seite 219]
1.9.1.4.1.1 - 13.32.4.1.1 By Formation of Two S--Se Bonds [Seite 219]
1.9.1.4.1.1.1 - 13.32.4.1.1.1 Method 1: Reactions of Arene-1,2-dithiols with Selenium Dioxide [Seite 219]
1.9.1.4.2 - 13.32.4.2 Synthesis by Ring Transformation [Seite 220]
1.9.1.4.2.1 - 13.32.4.2.1 Method 1: Reactions of 1,3,2-Benzodithiastannoles with Selenium Oxychloride, Trimethylsilyl Trifluoromethanesulfonate, and Samarium(II) Iodide [Seite 220]
1.9.1.5 - 13.32.5 Product Subclass 5: 1,2,3-Benzothiadiselenoles [Seite 221]
1.9.1.5.1 - 13.32.5.1 Synthesis by Ring Transformation [Seite 221]
1.9.1.5.1.1 - 13.32.5.1.1 Method 1: Synthesis from 1,3,2-Benzothiaselenastannoles with Selenium Oxychloride, Trimethylsilyl Trifluoromethanesulfonate, and Samarium(II) Iodide [Seite 221]
1.9.1.5.1.2 - 13.32.5.1.2 Method 2: Ring Contraction of Dibenzo-1,2,5,6- and 1,5,2,6-Dithiadiselenocins by Photolysis [Seite 222]
1.9.1.6 - 13.32.6 Product Subclass 6: 2,1,3-Benzothiadiselenoles [Seite 222]
1.9.1.6.1 - 13.32.6.1 Synthesis by Ring Transformation [Seite 222]
1.9.1.6.1.1 - 13.32.6.1.1 Method 1: Synthesis from 1,3,2-Benzodiselenastannoles [Seite 222]
1.9.1.6.1.1.1 - 13.32.6.1.1.1 Variation 1: Reactions with Sulfur in Liquid Ammonia [Seite 222]
1.9.1.6.1.1.2 - 13.32.6.1.1.2 Variation 2: Reactions with Thionyl Chloride, Sodium Iodide, and Perchloric Acid [Seite 223]
1.9.1.6.1.2 - 13.32.6.1.2 Method 2: Synthesis from 1,2,3-Benzotriselenoles with Sulfur [Seite 224]
1.9.1.7 - 13.32.7 Product Subclass 7: 1,2,3-Benzotriselenoles [Seite 224]
1.9.1.7.1 - 13.32.7.1 Synthesis by Ring-Closure Reactions [Seite 224]
1.9.1.7.1.1 - 13.32.7.1.1 By Formation of Two Se--Se Bonds [Seite 224]
1.9.1.7.1.1.1 - 13.32.7.1.1.1 Method 1: Synthesis from Dilithium Arene-1,2-diselenolates with Selenium Tetrachloride [Seite 224]
1.9.1.7.1.1.2 - 13.32.7.1.1.2 Method 2: Synthesis from Benzene-1,2-diselenenyl Dichloride with Selenium [Seite 225]
1.9.1.7.1.2 - 13.32.7.1.2 By Formation of Two Se--C Bonds [Seite 225]
1.9.1.7.1.2.1 - 13.32.7.1.2.1 Method 1: Synthesis from 1,2-Dibromoarenes with Selenium [Seite 225]
1.9.1.7.1.2.2 - 13.32.7.1.2.2 Method 2: Reactions of Tribenzo-1,4,7-trimercuronins with Selenium [Seite 226]
1.9.1.7.2 - 13.32.7.2 Synthesis by Ring Transformation [Seite 227]
1.9.1.7.2.1 - 13.32.7.2.1 Method 1: Synthesis from 1,3,2-Benzodiselenastannoles [Seite 227]
1.9.1.7.2.1.1 - 13.32.7.2.1.1 Variation 1: Reactions with Selenium Oxychloride, Trimethylsilyl Trifluoromethanesulfonate, and Samarium(II) Iodide [Seite 227]
1.9.1.7.2.1.2 - 13.32.7.2.1.2 Variation 2: Reaction with Selenium Tetrachloride [Seite 228]
1.9.1.7.2.2 - 13.32.7.2.2 Method 2: Reactions of 1,2,3-Benzoselenadiazoles with Selenium [Seite 228]
1.9.1.7.2.3 - 13.32.7.2.3 Method 3: By Ring Contraction [Seite 228]
1.9.1.7.2.3.1 - 13.32.7.2.3.1 Variation 1: Synthesis from Dibenzo-1,2,5,6-tetraselenocins by Photolysis [Seite 228]
1.9.1.7.2.3.2 - 13.32.7.2.3.2 Variation 2: Synthesis from Dibenzo-1,2,5,6-tetraselenocin with Diselenium Dichloride [Seite 229]
1.9.1.7.3 - 13.32.7.3 Synthesis by Substituent Modification [Seite 229]
1.9.1.7.3.1 - 13.32.7.3.1 One-Electron Oxidation [Seite 229]
1.9.1.7.3.1.1 - 13.32.7.3.1.1 Method 1: Synthesis from 1,2,3-Benzotriselenoles with Nitrosonium Hexafluorophosphate To Give Radical Cationic Salts [Seite 229]
1.9.1.8 - 13.32.8 Product Subclass 8: 1,2,3-Benzodithiatelluroles [Seite 230]
1.9.1.8.1 - 13.32.8.1 Synthesis by Ring Transformation [Seite 230]
1.9.1.8.1.1 - 13.32.8.1.1 Method 1: Synthesis from 1,3,2-Benzothiatelluratitanoles with Sulfur Dichloride [Seite 230]
1.9.1.9 - 13.32.9 Product Subclass 9: 1,3,2-Dithiatelluroles and 1,3,2-Benzodithiatelluroles [Seite 231]
1.9.1.9.1 - 13.32.9.1 Synthesis by Ring-Closure Reactions [Seite 231]
1.9.1.9.1.1 - 13.32.9.1.1 By Formation of Two S--Te Bonds [Seite 231]
1.9.1.9.1.1.1 - 13.32.9.1.1.1 Method 1: Synthesis from Arene-1,2-dithiols with Tellurium Tetrachloride [Seite 231]
1.9.1.9.1.1.2 - 13.32.9.1.1.2 Method 2: Synthesis from Metal Enedithiolates [Seite 232]
1.9.1.9.1.1.2.1 - 13.32.9.1.1.2.1 Variation 1: Reactions with Tellurium Tetrahalides [Seite 232]
1.9.1.9.1.1.2.2 - 13.32.9.1.1.2.2 Variation 2: Reactions with Sodium Tellurapentathionate [Seite 232]
1.9.1.9.2 - 13.32.9.2 Synthesis by Ring Transformation [Seite 233]
1.9.1.9.2.1 - 13.32.9.2.1 Method 1: Synthesis from 1,3,2-Benzodithiastannoles with Tellurium Tetrachloride [Seite 233]
1.9.1.10 - 13.32.10 Product Subclass 10: 1,2,3-Benzothiaselenatelluroles [Seite 234]
1.9.1.10.1 - 13.32.10.1 Synthesis by Ring Transformation [Seite 234]
1.9.1.10.1.1 - 13.32.10.1.1 Method 1: Synthesis from 1,3,2-Benzothiatelluratitanoles with Selenium Oxychloride [Seite 234]
1.9.1.11 - 13.32.11 Product Subclass 11: 1,3,2-Benzothiaselenatelluroles [Seite 235]
1.9.1.11.1 - 13.32.11.1 Synthesis by Ring Transformation [Seite 235]
1.9.1.11.1.1 - 13.32.11.1.1 Method 1: Synthesis from 1,3,2-Benzothiaselenastannoles with Tellurium Tetrachloride [Seite 235]
1.9.1.12 - 13.32.12 Product Subclass 12: 2,1,3-Benzothiaselenatelluroles [Seite 235]
1.9.1.12.1 - 13.32.12.1 Synthesis by Ring Transformation [Seite 235]
1.9.1.12.1.1 - 13.32.12.1.1 Method 1: Synthesis from a 1,3,2-Benzoselenatelluratitanole with Sulfur Dichloride [Seite 235]
1.9.1.13 - 13.32.13 Product Subclass 13: 1,2,3-Benzodiselenatelluroles [Seite 236]
1.9.1.13.1 - 13.32.13.1 Synthesis by Ring Transformation [Seite 236]
1.9.1.13.1.1 - 13.32.13.1.1 Method 1: Synthesis from 1,3,2-Benzoselenatelluratitanoles with Selenium Oxychloride [Seite 236]
1.9.1.14 - 13.32.14 Product Subclass 14: 1,3,2-Benzodiselenatelluroles [Seite 236]
1.9.2 - 13.33 Product Class 33: 1,2,4-Triazolium Salts [Seite 240]
1.9.2.1 - 13.33.1 Synthesis by Ring-Closure Reactions [Seite 241]
1.9.2.1.1 - 13.33.1.1 By Formation of Two N--C Bonds [Seite 241]
1.9.2.1.1.1 - 13.33.1.1.1 Formation of the N2--C3 and N4--C5 Bonds [Seite 241]
1.9.2.1.1.1.1 - 13.33.1.1.1.1 Method 1: Reaction of an Imidoyl Chloride with an N-Formylhydrazine [Seite 241]
1.9.2.1.1.2 - 13.33.1.1.2 Formation of the N1--C5 and N4--C5 Bonds [Seite 242]
1.9.2.1.1.2.1 - 13.33.1.1.2.1 Method 1: Reaction of an a-Aminohydrazone with a Trialkyl Orthoformate [Seite 242]
1.9.2.1.1.2.1.1 - 13.33.1.1.2.1.1 Variation 1: Reaction Using a One-Pot Protocol [Seite 242]
1.9.2.1.1.2.1.2 - 13.33.1.1.2.1.2 Variation 2: Reaction Using an Electron-Deficient Arylhydrazine [Seite 243]
1.9.2.1.1.2.1.3 - 13.33.1.1.2.1.3 Variation 3: Synthesis of N-Mesityl-Substituted Triazolium Salts [Seite 244]
1.9.2.1.1.2.1.4 - 13.33.1.1.2.1.4 Variation 4: Reaction Using Dimethyl Sulfate as the Amide-Activating Agent [Seite 246]
1.9.2.1.1.2.1.5 - 13.33.1.1.2.1.5 Variation 5: Synthesis of 2-Alkyl-[1,2,4]triazolo[4,3-a]pyridinium Salts [Seite 247]
1.9.2.1.1.2.1.6 - 13.33.1.1.2.1.6 Variation 6: Synthesis of 2-Aryl-[1,2,4]triazolo[4,3-a]pyridinium Salts [Seite 248]
1.9.2.2 - 13.33.2 Synthesis by Ring Transformation [Seite 248]
1.9.2.2.1 - 13.33.2.1 Formal Exchange of Ring Members with Retention of Ring Size [Seite 248]
1.9.2.2.1.1 - 13.33.2.1.1 Method 1: Synthesis from 1,3,4-Oxadiazolium Salts [Seite 248]
1.9.2.2.1.2 - 13.33.2.1.2 Method 2: Synthesis from 1,3,4-Thiadiazolium Salts [Seite 250]
1.9.2.3 - 13.33.3 Synthesis by Substituent Modification [Seite 251]
1.9.2.3.1 - 13.33.3.1 Addition Reactions [Seite 251]
1.9.2.3.1.1 - 13.33.3.1.1 Addition of Organic Groups [Seite 251]
1.9.2.3.1.1.1 - 13.33.3.1.1.1 Method 1: Alkylation Using an Alkyl Chloride, Bromide, or Iodide [Seite 251]
1.9.2.3.1.1.2 - 13.33.3.1.1.2 Method 2: Alkylation Using a Trialkyloxonium Tetrafluoroborate [Seite 251]
1.9.2.3.2 - 13.33.3.2 Modification of Substituents [Seite 252]
1.9.2.3.2.1 - 13.33.3.2.1 Method 1: Paal-Knorr Pyrrole Synthesis Using an Amine-Functionalized Triazolium Salt [Seite 252]
1.9.2.3.2.2 - 13.33.3.2.2 Method 2: Modification by Anion Exchange [Seite 253]
1.9.2.3.2.2.1 - 13.33.3.2.2.1 Variation 1: Of 1,2,4-Triazolium Halides [Seite 253]
1.9.2.3.2.2.2 - 13.33.3.2.2.2 Variation 2: With Silver Salts [Seite 254]
1.9.3 - 13.34 Product Class 34: Dithiadiazolium Salts and Dithiadiazolyl-Containing Compounds [Seite 256]
1.9.3.1 - 13.34.1 Product Subclass 1: 1,2,3,5-Dithiadiazolium Salts and Related Compounds [Seite 258]
1.9.3.1.1 - 13.34.1.1 Synthesis by Ring-Closure Reactions [Seite 259]
1.9.3.1.1.1 - 13.34.1.1.1 By Formation of One S--S and Two S--N Bonds [Seite 259]
1.9.3.1.1.1.1 - 13.34.1.1.1.1 Method 1: Synthesis from Amidines Using Sulfur Halides [Seite 259]
1.9.3.1.1.1.1.1 - 13.34.1.1.1.1.1 Variation 1: Reaction of Amidinium Salts with Sulfur Dichloride and 1,8-Diazabicyclo[5.4.0]undec-7-ene [Seite 259]
1.9.3.1.1.1.1.2 - 13.34.1.1.1.1.2 Variation 2: Reaction of Amidinium Salts with Sulfur Monochloride [Seite 260]
1.9.3.1.1.1.1.3 - 13.34.1.1.1.1.3 Variation 3: Reaction of N,N,N'-Tris(trimethylsilyl)amidines with Sulfur Dichloride [Seite 260]
1.9.3.1.1.1.2 - 13.34.1.1.1.2 Method 2: Reaction of Amidoximes with Sulfur Dichloride [Seite 261]
1.9.3.1.1.2 - 13.34.1.1.2 By Formation of One S--S, One S--N, and One N--C Bond [Seite 262]
1.9.3.1.1.2.1 - 13.34.1.1.2.1 Method 1: Synthesis from Nitriles [Seite 262]
1.9.3.1.1.2.1.1 - 13.34.1.1.2.1.1 Variation 1: Reaction with Sulfur Dichloride and Ammonium Chloride [Seite 262]
1.9.3.1.1.2.1.2 - 13.34.1.1.2.1.2 Variation 2: Reaction with Trithiazyl Trichloride [Seite 263]
1.9.3.1.1.2.2 - 13.34.1.1.2.2 Method 2: Synthesis from Azines Using Trithiazyl Trichloride [Seite 263]
1.9.3.1.1.3 - 13.34.1.1.3 By Formation of One S--S and Two N--C Bonds [Seite 264]
1.9.3.1.1.3.1 - 13.34.1.1.3.1 Method 1: Synthesis from Alkenes Using Trithiazyl Trichloride [Seite 264]
1.9.3.1.2 - 13.34.1.2 Synthesis by Ring Transformation [Seite 264]
1.9.3.1.2.1 - 13.34.1.2.1 Method 1: Synthesis by One-Electron Reduction Using Zinc/Copper or Triphenylstibine [Seite 264]
1.9.3.1.2.2 - 13.34.1.2.2 Method 2: Synthesis from 1,3-Dichloro-1,3,2,4,6-dithiatriazines by Thermolytic Ring Contraction [Seite 265]
1.9.3.2 - 13.34.2 Product Subclass 2: 1,3,2,4-Dithiadiazolium Salts and Related Compounds [Seite 266]
1.9.3.2.1 - 13.34.2.1 Synthesis by Ring-Closure Reactions [Seite 267]
1.9.3.2.1.1 - 13.34.2.1.1 By Formation of One S--N and One S--C Bond [Seite 267]
1.9.3.2.1.1.1 - 13.34.2.1.1.1 Method 1: Synthesis from Nitriles with Dithionitronium Hexafluoroarsenate [Seite 267]
1.9.3.2.1.2 - 13.34.2.1.2 By Formation of One S--N and One N--C Bond [Seite 269]
1.9.3.2.1.2.1 - 13.34.2.1.2.1 Method 1: Synthesis from Bifunctional Acyl Chlorides with an N,N'-Bis(trimethylsilyl)sulfur Diimide [Seite 269]
1.9.3.2.2 - 13.34.2.2 Synthesis by Ring Transformation [Seite 270]
1.9.3.2.2.1 - 13.34.2.2.1 Method 1: Synthesis by One-Electron Reduction Using Triphenylstibine [Seite 270]
1.9.3.2.2.2 - 13.34.2.2.2 Method 2: Synthesis from a Dithiadiazastannole Using Carbonyl Difluoride [Seite 270]
1.9.3.2.3 - 13.34.2.3 Synthesis by Substituent Modification [Seite 271]
1.9.3.2.3.1 - 13.34.2.3.1 Method 1: Synthesis by O-Alkylation Using Methyl Fluorosulfonate [Seite 271]
1.10 - Volume 16: Six-Membered Hetarenes with Two Identical Heteroatoms [Seite 274]
1.10.1 - 16.4 Product Class 4: 1,4-Dithiins [Seite 274]
1.10.1.1 - 16.4.6 1,4-Dithiins [Seite 274]
1.10.1.1.1 - 16.4.6.1 Synthesis by Ring-Closure Reactions [Seite 276]
1.10.1.1.1.1 - 16.4.6.1.1 By Formation of Four S--C Bonds [Seite 276]
1.10.1.1.1.1.1 - 16.4.6.1.1.1 Fragments C--C, C--C, and Two S Fragments [Seite 276]
1.10.1.1.1.1.1.1 - 16.4.6.1.1.1.1 Method 1: Synthesis from (Z)-1,2-Dichloroethene and Sodium Sulfide [Seite 276]
1.10.1.1.1.1.1.2 - 16.4.6.1.1.1.2 Method 2: Synthesis from Alkynes and Sulfur [Seite 277]
1.10.1.1.1.2 - 16.4.6.1.2 By Formation of Two S--C Bonds [Seite 277]
1.10.1.1.1.2.1 - 16.4.6.1.2.1 Fragments C--C--S--C--C and S [Seite 277]
1.10.1.1.1.2.1.1 - 16.4.6.1.2.1.1 Method 1: Synthesis from 1-Bromo-4-phenoxybut-2-yne and Sodium Sulfide [Seite 277]
1.10.1.1.1.2.2 - 16.4.6.1.2.2 Fragments S--C--C--S and C--C [Seite 278]
1.10.1.1.1.2.2.1 - 16.4.6.1.2.2.1 Method 1: Synthesis from 1,2-Dihydroxyarenes and 1,2-Dithiols [Seite 278]
1.10.1.1.1.2.2.2 - 16.4.6.1.2.2.2 Method 2: Synthesis from 1,2,3,4,5-Benzopentathiepin and Active Methylene Compounds [Seite 279]
1.10.1.1.1.2.2.3 - 16.4.6.1.2.2.3 Method 3: Synthesis from 1,2,3,4,5-Pentathiepins and Alkynes [Seite 280]
1.10.1.1.1.2.3 - 16.4.6.1.2.3 Fragments S--C--C and S--C--C [Seite 281]
1.10.1.1.1.2.3.1 - 16.4.6.1.2.3.1 Method 1: Thermolysis of 1,2,3-Thiadiazoles [Seite 281]
1.10.1.1.1.2.3.2 - 16.4.6.1.2.3.2 Method 2: Synthesis from 4-(Alkylamino)-4-oxobutanoic Acids and Thionyl Chloride [Seite 283]
1.10.1.1.1.3 - 16.4.6.1.3 By Formation of One S--C Bond [Seite 284]
1.10.1.1.1.3.1 - 16.4.6.1.3.1 Fragment S--C--C--S--C--C [Seite 284]
1.10.1.1.1.3.1.1 - 16.4.6.1.3.1.1 Method 1: Synthesis from 2-Chloro-1-phenylethane-1,1-dithiol and Sodium Sulfide [Seite 284]
1.10.1.1.1.3.1.2 - 16.4.6.1.3.1.2 Method 2: Synthesis from 1,8-Diketones [Seite 285]
1.10.1.1.2 - 16.4.6.2 Synthesis by Ring Transformation [Seite 286]
1.10.1.1.2.1 - 16.4.6.2.1 By Ring Contraction [Seite 286]
1.10.1.1.2.1.1 - 16.4.6.2.1.1 Method 1: Synthesis by Photolysis of Unsaturated 18-Membered Thia-Crown Ethers [Seite 286]
1.10.1.1.2.1.2 - 16.4.6.2.1.2 Method 2: Synthesis by Pummerer Dehydration of 3,8-Dihydro-1,2,5,6-dithiadiazocine 1-Oxides [Seite 286]
1.10.1.1.3 - 16.4.6.3 Aromatization-Type Reactions [Seite 287]
1.10.1.1.3.1 - 16.4.6.3.1 By Elimination [Seite 287]
1.10.1.1.3.1.1 - 16.4.6.3.1.1 Method 1: Synthesis from 2-Chloro- and 2,3-Dichloro-1,4-dithianes [Seite 287]
1.10.1.1.3.1.2 - 16.4.6.3.1.2 Method 2: Synthesis from 1,4-Dithiane-2,5-diol [Seite 288]
1.10.1.1.4 - 16.4.6.4 Synthesis by Substituent Modification [Seite 289]
1.10.1.1.4.1 - 16.4.6.4.1 Substitution of Existing Substituents [Seite 289]
1.10.1.1.4.1.1 - 16.4.6.4.1.1 Of Hydrogen [Seite 289]
1.10.1.1.4.1.1.1 - 16.4.6.4.1.1.1 Method 1: Introduction of Alkyl and Carboxamide Groups by Radical Substitution [Seite 289]
1.10.1.1.4.2 - 16.4.6.4.2 Rearrangement of Substituents [Seite 291]
1.10.1.1.4.2.1 - 16.4.6.4.2.1 Method 1: Isomerization of 1,4-Dithiins via Ring-Opening-Ring-Closing Reactions [Seite 291]
1.10.1.1.4.3 - 16.4.6.4.3 Modification of Substituents [Seite 292]
1.10.1.1.4.3.1 - 16.4.6.4.3.1 Modification of Sulfur Substituents [Seite 292]
1.10.1.1.4.3.1.1 - 16.4.6.4.3.1.1 Method 1: Ring Opening of Acenaphtho[1,2-b][1,3]dithiolo[4,5-e][1,4]dithiin-9-one with Potassium tert-Butoxide [Seite 292]
1.10.1.1.4.3.1.2 - 16.4.6.4.3.1.2 Method 2: Synthesis of Tin Dithiolates from Ketones by Grignard Reaction [Seite 293]
1.10.2 - 16.18 Product Class 18: Pyridopyridazines [Seite 296]
1.10.2.1 - 16.18.7 Pyridopyridazines [Seite 296]
1.10.2.1.1 - 16.18.7.1 Pyrido[2,3-c]pyridazines [Seite 298]
1.10.2.1.1.1 - 16.18.7.1.1 Synthesis by Ring-Closure Reactions [Seite 298]
1.10.2.1.1.1.1 - 16.18.7.1.1.1 By Formation of One N--C and One C--C Bond [Seite 298]
1.10.2.1.1.1.1.1 - 16.18.7.1.1.1.1 Method 1: Cyclization of 3-Aminopyridazine-4-carbonitrile with Malonates [Seite 298]
1.10.2.1.1.1.2 - 16.18.7.1.1.2 By Formation of One N--N Bond [Seite 298]
1.10.2.1.1.1.2.1 - 16.18.7.1.1.2.1 Method 1: Annulation of 3-(2-Nitrophenyl)quinolin-2-amine [Seite 298]
1.10.2.1.2 - 16.18.7.2 Pyrido[2,3-d]pyridazines [Seite 300]
1.10.2.1.2.1 - 16.18.7.2.1 Synthesis by Ring-Closure Reactions [Seite 300]
1.10.2.1.2.1.1 - 16.18.7.2.1.1 By Formation of Two N--C Bonds [Seite 300]
1.10.2.1.2.1.1.1 - 16.18.7.2.1.1.1 Method 1: Condensation of Hydrazine with a Dicarbonyl-Functionalized Piperidinone Scaffold [Seite 300]
1.10.2.1.2.1.1.2 - 16.18.7.2.1.1.2 Method 2: Condensation of Hydrazine with 2-Formylquinoline-3-carboxylate [Seite 301]
1.10.2.1.2.1.1.3 - 16.18.7.2.1.1.3 Method 3: Incorporating a (2-Formylpyridin-3-yl)copper Reagent in Pyrido[2,3-d]pyridazine Synthesis [Seite 302]
1.10.2.1.2.1.1.4 - 16.18.7.2.1.1.4 Method 4: Suzuki Cross Coupling of Chloro(methoxy)pyridazin-3(2H)-ones [Seite 304]
1.10.2.1.2.1.1.5 - 16.18.7.2.1.1.5 Method 5: Condensation of 5,6-Dicarbonyl-Functionalized Pyridinones with Hydrazine [Seite 305]
1.10.2.1.2.1.2 - 16.18.7.2.1.2 By Formation of One N--C and One C--C Bond [Seite 307]
1.10.2.1.2.1.2.1 - 16.18.7.2.1.2.1 Method 1: Condensation of Acetone with 5-Acetyl-4-amino-6-phenylpyridazin-3(2H)-one [Seite 307]
1.10.2.1.2.2 - 16.18.7.2.2 Synthesis by Ring Transformation [Seite 308]
1.10.2.1.2.2.1 - 16.18.7.2.2.1 By Ring Enlargement [Seite 308]
1.10.2.1.2.2.1.1 - 16.18.7.2.2.1.1 Method 1: Condensation of Hydrazine with Pyridine-2,3-dicarboxylic Anhydride and 3-Benzoylpicolinic Acid [Seite 308]
1.10.2.1.2.2.1.2 - 16.18.7.2.2.1.2 Method 2: Condensation of Hydrazine with Pyrrolo[3,4-c]pyridinone [Seite 311]
1.10.2.1.3 - 16.18.7.3 Pyrido[3,2-c]pyridazines [Seite 313]
1.10.2.1.3.1 - 16.18.7.3.1 Synthesis by Ring-Closure Reactions [Seite 313]
1.10.2.1.3.1.1 - 16.18.7.3.1.1 By Formation of One N--N Bond [Seite 313]
1.10.2.1.3.1.1.1 - 16.18.7.3.1.1.1 Method 1: Condensation and Reduction of 2-Amino-2'-nitrobiaryls [Seite 313]
1.10.2.1.4 - 16.18.7.4 Pyrido[3,4-c]pyridazines [Seite 313]
1.10.2.1.4.1 - 16.18.7.4.1 Synthesis by Ring-Closure Reactions [Seite 313]
1.10.2.1.4.1.1 - 16.18.7.4.1.1 By Formation of One N--N and One N--C Bond [Seite 313]
1.10.2.1.4.1.1.1 - 16.18.7.4.1.1.1 Method 1: Intramolecular Diazo Coupling of 4-Hetarylpyridin-3-amines [Seite 313]
1.10.2.1.5 - 16.18.7.5 Pyrido[3,4-d]pyridazines [Seite 315]
1.10.2.1.5.1 - 16.18.7.5.1 Synthesis by Ring Transformation [Seite 315]
1.10.2.1.5.1.1 - 16.18.7.5.1.1 By Ring Enlargement [Seite 315]
1.10.2.1.5.1.1.1 - 16.18.7.5.1.1.1 Method 1: Condensation of Hydrazine with 1H-Pyrrolo[3,4-c]pyridine-1,3(2H)-dione [Seite 315]
1.10.2.1.5.1.1.2 - 16.18.7.5.1.1.2 Method 2: Ring Expansion of Pyrazolopyridines [Seite 316]
1.10.2.1.5.1.1.3 - 16.18.7.5.1.1.3 Method 3: Insertion of Hydrazine into (Z)-3-Benzylidenefuro[3,4-c]pyridin-1(3H)-ones [Seite 317]
1.10.2.1.6 - 16.18.7.6 Pyrido[4,3-c]pyridazines [Seite 319]
1.10.2.1.6.1 - 16.18.7.6.1 Synthesis by Ring-Closure Reactions [Seite 319]
1.10.2.1.6.1.1 - 16.18.7.6.1.1 By Formation of One N--C and One C--C Bond [Seite 319]
1.10.2.1.6.1.1.1 - 16.18.7.6.1.1.1 Method 1: Fusion of an Aminouracil with a Chloropyridazinecarbonitrile or Pyridazines Having Vicinal Chloro and Carbonyl Groups [Seite 319]
1.10.3 - 16.19 Product Class 19: Pyridopyrimidines [Seite 322]
1.10.3.1 - 16.19.5 Pyridopyrimidines [Seite 322]
1.10.3.1.1 - 16.19.5.1 Pyrido[2,3-d]pyrimidines [Seite 323]
1.10.3.1.1.1 - 16.19.5.1.1 By Formation of Three N--C Bonds and One C--C Bond [Seite 323]
1.10.3.1.1.1.1 - 16.19.5.1.1.1 Method 1: Cyclization of Acrylates, Functionalized Nitriles, and Guanidines or Amidines [Seite 323]
1.10.3.1.1.2 - 16.19.5.1.2 By Formation of One N--C and Two C--C Bonds [Seite 324]
1.10.3.1.1.2.1 - 16.19.5.1.2.1 Method 1: Cyclization of 2-Heterosubstituted 6-Aminopyrimidin-4(3H)-ones, Aldehydes, and Active Methylene Compounds [Seite 324]
1.10.3.1.1.3 - 16.19.5.1.3 By Formation of Two N--C Bonds [Seite 328]
1.10.3.1.1.3.1 - 16.19.5.1.3.1 Method 1: Cyclization of 2-Nitrogen-Functionalized Nicotinamides [Seite 328]
1.10.3.1.1.4 - 16.19.5.1.4 By Formation of One N--C and One C--C Bond [Seite 332]
1.10.3.1.1.4.1 - 16.19.5.1.4.1 Method 1: Cyclization of Pyrimidin-4-amines with a,ß-Unsaturated Carbonyl Compounds and Related Species [Seite 332]
1.10.3.1.1.5 - 16.19.5.1.5 By Formation of One N--C Bond [Seite 336]
1.10.3.1.1.5.1 - 16.19.5.1.5.1 Method 1: Dehydrative Cyclization of 2-Acetamidonicotinamides [Seite 336]
1.10.3.1.1.5.2 - 16.19.5.1.5.2 Method 2: Cyclization of 5-(4-Aminopyrimidin-5-yl)-1H-imidazole-4-carbonitriles [Seite 337]
1.10.3.1.1.6 - 16.19.5.1.6 By Formation of One C--C Bond [Seite 338]
1.10.3.1.1.6.1 - 16.19.5.1.6.1 Method 1: Palladium-Catalyzed Intramolecular Arylation of 4-(2-Bromobenzylamino)pyrimidines [Seite 338]
1.10.3.1.2 - 16.19.5.2 Pyrido[3,2-d]pyrimidines [Seite 339]
1.10.3.1.2.1 - 16.19.5.2.1 By Formation of Three N--C Bonds [Seite 339]
1.10.3.1.2.1.1 - 16.19.5.2.1.1 Method 1: Cycloamination of 3-Isocyanatopyridine-2-carboxylates [Seite 339]
1.10.3.1.2.2 - 16.19.5.2.2 By Formation of One C--C Bond [Seite 341]
1.10.3.1.2.2.1 - 16.19.5.2.2.1 Method 1: Palladium-Catalyzed Intramolecular Arylation of 5-(2-Halobenzylamino)pyrimidines [Seite 341]
1.10.3.1.3 - 16.19.5.3 Pyrido[3,4-d]pyrimidines [Seite 342]
1.10.3.1.3.1 - 16.19.5.3.1 By Formation of Two N--C Bonds [Seite 342]
1.10.3.1.3.1.1 - 16.19.5.3.1.1 Method 1: Cyclization of 3-Nitrogen-Functionalized Pyridine-4-carboxylic Acids with Nitrogen-Containing Compounds [Seite 342]
1.10.3.1.3.2 - 16.19.5.3.2 By Formation of One N--C and One C--C Bond [Seite 342]
1.10.3.1.3.2.1 - 16.19.5.3.2.1 Method 1: Suzuki Coupling/Condensation of 5-Bromopyrimidine-4-carboxylates with (2-Aminophenyl)boronic Acids [Seite 342]
1.10.3.1.4 - 16.19.5.4 Pyrido[4,3-d]pyrimidines [Seite 343]
1.10.3.1.4.1 - 16.19.5.4.1 By Formation of Two N--C Bonds and One C--C Bond [Seite 343]
1.10.3.1.4.1.1 - 16.19.5.4.1.1 Method 1: Cyclization of 1-Benzylpiperidin-4-one, Nitriles, and Trifluoromethanesulfonic Anhydride [Seite 343]
1.10.3.1.4.2 - 16.19.5.4.2 By Formation of Two N--C Bonds [Seite 344]
1.10.3.1.4.2.1 - 16.19.5.4.2.1 Method 1: Cyclization of 4-(Arylethynyl)pyrimidine-5-carbaldehydes with tert-Butylamine [Seite 344]
1.10.3.1.4.2.2 - 16.19.5.4.2.2 Method 2: Cycloamination of N-(3-Acetylpyridin-4-yl)formimidates with Primary Amines [Seite 345]
1.10.4 - 16.21 Product Class 21: Pteridines and Related Structures [Seite 348]
1.10.4.1 - 16.21.4 Pteridines and Related Structures [Seite 348]
1.10.4.1.1 - 16.21.4.1 Synthesis by Ring-Closure Reactions [Seite 348]
1.10.4.1.1.1 - 16.21.4.1.1 By Annulation to the Pyrimidine Ring [Seite 348]
1.10.4.1.1.1.1 - 16.21.4.1.1.1 By Formation of Two N--C Bonds [Seite 348]
1.10.4.1.1.1.1.1 - 16.21.4.1.1.1.1 Fragments N--C--C--N and C--C [Seite 348]
1.10.4.1.1.1.1.1.1 - 16.21.4.1.1.1.1.1 Method 1: Synthesis from Pyrimidine-4,5-diamines and Diketones [Seite 348]
1.10.4.1.1.1.1.1.2 - 16.21.4.1.1.1.1.2 Method 2: Synthesis from Pyrimidine-4,5-diamines and 1,2,3-Tricarbonyl Compounds [Seite 349]
1.10.4.1.1.1.1.1.3 - 16.21.4.1.1.1.1.3 Method 3: Synthesis from Pyrimidine-4,5-diamines and Modified 1,2-Dicarbonyl Systems [Seite 349]
1.10.4.1.1.1.1.1.4 - 16.21.4.1.1.1.1.4 Method 4: Synthesis from 5-Nitrosopyrimidin-4-amines and a,ß-Unsaturated Acyl Halides [Seite 351]
1.10.4.1.1.1.1.2 - 16.21.4.1.1.1.2 Fragments N--C--C and N--C--C [Seite 352]
1.10.4.1.1.1.1.2.1 - 16.21.4.1.1.1.2.1 Method 1: From 4-Chloro-5-nitropyrimidines and a-Aminocarbonyl Compounds (Polonovski-Boon Reaction) [Seite 352]
1.10.4.1.1.1.1.2.2 - 16.21.4.1.1.1.2.2 Method 2: From 4-Iodopyrimidin-5-amine and 1H-Pyrrole-2-carbaldehyde [Seite 353]
1.10.4.1.1.2 - 16.21.4.1.2 By Annulation to the Pyrazine Ring [Seite 354]
1.10.4.1.1.2.1 - 16.21.4.1.2.1 By Formation of Two N--C Bonds [Seite 354]
1.10.4.1.1.2.1.1 - 16.21.4.1.2.1.1 Fragments N--C--C--C--N and C [Seite 354]
1.10.4.1.1.2.1.1.1 - 16.21.4.1.2.1.1.1 Method 1: From 2,3-Disubstituted Pyrazines and One-Carbon Units [Seite 354]
1.10.4.1.2 - 16.21.4.2 Synthesis by Ring Transformation [Seite 354]
1.10.4.1.2.1 - 16.21.4.2.1 Method 1: Synthesis by Ring Contraction of Pyrimidoazepine Derivatives [Seite 354]
1.10.4.1.3 - 16.21.4.3 Synthesis by Substituent Modification [Seite 355]
1.10.4.1.3.1 - 16.21.4.3.1 Substitution of Existing Substituents [Seite 355]
1.10.4.1.3.1.1 - 16.21.4.3.1.1 Substitution of Hydrogen [Seite 355]
1.10.4.1.3.1.1.1 - 16.21.4.3.1.1.1 Method 1: N-Alkylation of Pteridinones or Their Derivatives [Seite 355]
1.10.4.1.3.1.1.2 - 16.21.4.3.1.1.2 Method 2: Direct Introduction of Substituents by Nucleophilic Reactions [Seite 356]
1.10.4.1.3.1.2 - 16.21.4.3.1.2 Substitution of Heteroatoms [Seite 358]
1.10.4.1.3.1.2.1 - 16.21.4.3.1.2.1 Method 1: Substitution of Sulfur: Amination [Seite 358]
1.10.4.1.3.1.2.2 - 16.21.4.3.1.2.3 Method 2: Substitution of Halogens: Alkylation [Seite 361]
1.10.4.1.3.2 - 16.21.4.3.2 Modification of Substituents [Seite 362]
1.10.4.1.3.2.1 - 16.21.4.3.2.1 Method 1: Hydrolysis [Seite 362]
1.10.4.1.3.2.2 - 16.21.4.3.2.2 Method 2: Modification of Amine Substituents [Seite 362]
1.10.4.1.3.2.3 - 16.21.4.3.2.3 Method 3: Oxidation of Alkylsulfanyl Substituents [Seite 363]
1.10.4.1.3.3 - 16.21.4.3.3 Rearrangement of Substituents [Seite 363]
1.10.4.1.3.3.1 - 16.21.4.3.3.1 Method 1: Rearrangement of Allyl Groups [Seite 363]
1.10.5 - 16.22 Product Class 22: Other Diazinodiazines [Seite 366]
1.10.5.1 - 16.22.6 Other Diazinodiazines [Seite 366]
1.10.5.1.1 - 16.22.6.1 Pyridazinopyridazines [Seite 366]
1.10.5.1.1.1 - 16.22.6.1.1 Addition Reactions [Seite 366]
1.10.5.1.1.1.1 - 16.22.6.1.1.1 Method 1: Addition of Alkyl Groups [Seite 366]
1.10.5.1.2 - 16.22.6.2 Pyrimidopyridazines [Seite 367]
1.10.5.1.2.1 - 16.22.6.2.1 Synthesis by Ring-Closure Reactions [Seite 367]
1.10.5.1.2.1.1 - 16.22.6.2.1.1 By Annulation to an Arene [Seite 367]
1.10.5.1.2.1.1.1 - 16.22.6.2.1.1.1 By Formation of Two N--C Bonds [Seite 367]
1.10.5.1.2.1.1.1.1 - 16.22.6.2.1.1.1.1 Method 1: From Substituted Pyridazines [Seite 367]
1.10.5.1.2.1.1.1.2 - 16.22.6.2.1.1.1.2 Method 2: From Substituted Pyrimidines [Seite 368]
1.10.5.1.2.1.1.2 - 16.22.6.2.1.1.2 By Formation of One N--C and One C--C Bond [Seite 371]
1.10.5.1.2.1.1.2.1 - 16.22.6.2.1.1.2.1 Method 1: From 1,2-Dicarbonyl Compounds or a-Bromo Ketones [Seite 371]
1.10.5.1.2.1.1.3 - 16.22.6.2.1.1.3 By Formation of One N--C Bond [Seite 372]
1.10.5.1.2.1.1.3.1 - 16.22.6.2.1.1.3.1 Method 1: From 4,5-Disubstituted Pyrimidines [Seite 372]
1.10.5.1.2.2 - 16.22.6.2.2 Synthesis by Substituent Modification [Seite 373]
1.10.5.1.2.2.1 - 16.22.6.2.2.1 Substitution of Existing Substituents [Seite 373]
1.10.5.1.2.2.1.1 - 16.22.6.2.2.1.1 Method 1: By Substitution of Chlorine [Seite 373]
1.10.5.1.2.2.1.2 - 16.22.6.2.2.1.2 Method 2: By Substitution of Hydrogen [Seite 374]
1.10.5.1.2.3 - 16.22.6.2.3 Addition Reactions [Seite 374]
1.10.5.1.2.3.1 - 16.22.6.2.3.1 Method 1: Hydrogenation [Seite 374]
1.10.5.1.3 - 16.22.6.3 Pyrimidopyrimidines [Seite 375]
1.10.5.1.3.1 - 16.22.6.3.1 Synthesis by Ring-Closure Reactions [Seite 375]
1.10.5.1.3.1.1 - 16.22.6.3.1.1 By Annulation to an Arene [Seite 375]
1.10.5.1.3.1.1.1 - 16.22.6.3.1.1.1 By Formation of Two N--C Bonds [Seite 375]
1.10.5.1.3.1.1.1.1 - 16.22.6.3.1.1.1.1 Method 1: From 2,4,5-Trisubstituted Pyrimidines [Seite 375]
1.10.5.1.3.1.1.1.2 - 16.22.6.3.1.1.1.2 Method 2: From 4,5,6-Trisubstituted Pyrimidines [Seite 378]
1.10.5.1.3.1.1.1.3 - 16.22.6.3.1.1.1.3 Method 3: From 2,4,5,6-Tetrasubstituted Pyrimidines [Seite 380]
1.10.5.1.3.1.1.1.3.1 - 16.22.6.3.1.1.1.3.1 Variation 1: With a Guanidine or Thiourea [Seite 380]
1.10.5.1.3.1.1.1.3.2 - 16.22.6.3.1.1.1.3.2 Variation 2: With a Thiouronium Chloride and an Amine [Seite 381]
1.10.5.1.3.1.2 - 16.22.6.3.1.2 By Cycloaddition Reactions [Seite 382]
1.10.5.1.3.1.2.1 - 16.22.6.3.1.2.1 By Formation of Two N--C Bonds [Seite 382]
1.10.5.1.3.1.2.1.1 - 16.22.6.3.1.2.1.1 Method 1: By Diels-Alder Reaction [Seite 382]
1.10.5.1.3.1.2.2 - 16.22.6.3.1.2.2 By Formation of One N--C and One C--C Bond [Seite 382]
1.10.5.1.3.1.2.2.1 - 16.22.6.3.1.2.2.1 Method 1: By Diels-Alder Reaction [Seite 382]
1.10.5.1.3.1.2.2.1.1 - 16.22.6.3.1.2.2.1.1 Variation 1: From Methyl 6-Methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate [Seite 382]
1.10.5.1.3.1.2.2.1.2 - 16.22.6.3.1.2.2.1.2 Variation 2: From 6-Amino-1,3-dimethylpyrimidine-2,4(1H,3H)-diones [Seite 383]
1.10.5.1.3.2 - 16.22.6.3.2 Synthesis By Ring Transformation [Seite 384]
1.10.5.1.3.2.1 - 16.22.6.3.2.1 By Ring Enlargement [Seite 384]
1.10.5.1.3.2.1.1 - 16.22.6.3.2.1.1 Method 1: From Purine Skeletons [Seite 384]
1.10.5.1.3.3 - 16.22.6.3.3 Synthesis by Substituent Modification [Seite 386]
1.10.5.1.3.3.1 - 16.22.6.3.3.1 Modification of Existing Substituents [Seite 386]
1.10.5.1.3.3.1.1 - 16.22.6.3.3.1.1 Method 1: By Substitution of Chlorine [Seite 386]
1.10.5.1.3.3.1.2 - 16.22.6.3.3.1.2 Method 2: By Substitution of Sulfur-Containing Groups [Seite 387]
1.11 - Volume 17: Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles [Seite 390]
1.11.1 - 17.2 Product Class 2: Six-Membered Hetarenes with Three Heteroatoms [Seite 390]
1.11.1.1 - 17.2.1.9 1,2,3-Triazines and Phosphorus Analogues [Seite 390]
1.11.1.1.1 - 17.2.1.9.1 Monocyclic 1,2,3-Triazines [Seite 390]
1.11.1.1.1.1 - 17.2.1.9.1.1 Aromatization [Seite 390]
1.11.1.1.1.1.1 - 17.2.1.9.1.1.1 Method 1: Dehydrogenation and Oxidation of 2,5-Dihydro-1,2,3-triazines [Seite 390]
1.11.1.1.1.2 - 17.2.1.9.1.2 Synthesis by Substituent Modification [Seite 391]
1.11.1.1.1.2.1 - 17.2.1.9.1.2.1 Addition Reactions [Seite 391]
1.11.1.1.1.2.1.1 - 17.2.1.9.1.2.1.1 Method 1: Protonation of 1,2,3-Triazines by Tetrafluoroboric Acid [Seite 391]
1.11.1.1.1.2.1.2 - 17.2.1.9.1.2.1.2 Method 2: N-Acylation, N-Alkylation, and N-Arylation [Seite 392]
1.11.1.1.1.2.2 - 17.2.1.9.1.2.2 Modification of Substituents [Seite 394]
1.11.1.1.1.2.2.1 - 17.2.1.9.1.2.2.1 Method 1: Dipolar Cycloaddition with Dicyano(1,2,3-triazin-2-ium-2-yl)methanides [Seite 394]
1.11.1.1.1.2.2.2 - 17.2.1.9.1.2.2.2 Method 2: Dipolar Cycloaddition with 2-Ethyl-1,2,3-triazin-2-ium Salts [Seite 395]
1.11.1.1.1.3 - 17.2.1.9.1.3 Applications of Monocyclic 1,2,3-Triazines in Organic Synthesis [Seite 395]
1.11.1.1.1.3.1 - 17.2.1.9.1.3.1 Method 1: Synthesis of 2,5-Dihydro-1,2,3-triazines [Seite 395]
1.11.1.1.2 - 17.2.1.9.2 Annulated 1,2,3-Triazines [Seite 397]
1.11.1.1.2.1 - 17.2.1.9.2.1 Synthesis by Ring-Closure Reactions [Seite 397]
1.11.1.1.2.1.1 - 17.2.1.9.2.1.1 By Annulation to a Heterocycle or Carbocycle [Seite 397]
1.11.1.1.2.1.1.1 - 17.2.1.9.2.1.1.1 By Formation of Two N--N Bonds [Seite 397]
1.11.1.1.2.1.1.1.1 - 17.2.1.9.2.1.1.1.1 Method 1: Reaction of a 2-(4,5-Dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-3-amine with Nitrous Acid [Seite 397]
1.11.1.1.2.1.1.1.2 - 17.2.1.9.2.1.1.1.2 Method 2: Reaction of 2-Amino-1H-pyrrole-3,4-dicarboxamides with Nitrous Acid [Seite 398]
1.11.1.1.2.1.1.1.3 - 17.2.1.9.2.1.1.1.3 Method 3: Reaction of Amino-Substituted Pyridine- and Pyridazinecarboxamides with Nitrous Acid [Seite 399]
1.11.1.1.2.1.1.1.4 - 17.2.1.9.2.1.1.1.4 Method 4: Reaction of Amino-Substituted Hetarenecarbonitriles with Nitrous Acid and Hydrochloric Acid [Seite 400]
1.11.1.1.2.1.1.1.5 - 17.2.1.9.2.1.1.1.5 Method 5: Diazotization of (Aminohetaryl)azoles [Seite 404]
1.11.1.1.2.1.1.1.6 - 17.2.1.9.2.1.1.1.6 Method 6: Diazotization of 3,4-Diaminothieno[2,3-b]thiophene-2,5-dicarboxamide [Seite 405]
1.11.1.1.2.1.1.2 - 17.2.1.9.2.1.1.2 By Formation of One N--C Bond [Seite 405]
1.11.1.1.2.1.1.2.1 - 17.2.1.9.2.1.1.2.1 Method 1: Cyclization of 2-(Triaz-1-enyl)benzonitriles [Seite 405]
1.11.1.1.2.1.2 - 17.2.1.9.2.1.2 By Annulation to the 1,2,3-Triazine Ring [Seite 406]
1.11.1.1.2.1.2.1 - 17.2.1.9.2.1.2.1 By Formation of One C--C Bond [Seite 406]
1.11.1.1.2.1.2.1.1 - 17.2.1.9.2.1.2.1.1 Method 1: Condensation Reactions of Annulated 4-Hydrazino-1,2,3-triazines [Seite 406]
1.11.1.1.2.1.2.1.2 - 17.2.1.9.2.1.2.1.2 Method 2: Condensation Reactions of 4-Chloro-1,2,3-triazines [Seite 408]
1.11.1.1.2.2 - 17.2.1.9.2.2 Synthesis by Substituent Modification [Seite 410]
1.11.1.1.2.2.1 - 17.2.1.9.2.2.1 Substitution of Existing Substituents [Seite 410]
1.11.1.1.2.2.1.1 - 17.2.1.9.2.2.1.1 Of Hydrogen [Seite 410]
1.11.1.1.2.2.1.1.1 - 17.2.1.9.2.2.1.1.1 Method 1: N-Alkylation and N-Arylation [Seite 410]
1.11.1.1.2.2.1.2 - 17.2.1.9.2.2.1.2 Of Heteroatoms [Seite 410]
1.11.1.1.2.2.1.2.1 - 17.2.1.9.2.2.1.2.1 Method 1: Substitution of a 4-Chloro-Substitutent with Sulfur-Containing Groups [Seite 410]
1.11.1.1.2.2.1.2.2 - 17.2.1.9.2.2.1.2.2 Method 2: Substitution of a 4-Chloro-Substitutent with Amino or Hydrazino Groups [Seite 411]
1.11.1.1.2.2.1.2.3 - 17.2.1.9.2.2.1.2.3 Method 3: Substitution of a 4-Chloro-Substitutent with Sodium Azide [Seite 416]
1.11.1.1.2.2.1.2.4 - 17.2.1.9.2.2.1.2.4 Method 4: Substitution of a 4-Hydroxy Group by a Halogen [Seite 416]
1.11.1.1.2.2.1.2.5 - 17.2.1.9.2.2.1.2.5 Method 5: Substitution of Amino, 4-Hydrazino, and 4-(1H-1,2,4-Triazol-1-yl) Groups [Seite 417]
1.11.1.1.2.2.2 - 17.2.1.9.2.2.2 Modification of Substituents [Seite 419]
1.11.1.1.2.2.2.1 - 17.2.1.9.2.2.2.1 Method 1: Modification of Nitrogen Functionality [Seite 419]
1.11.1.2 - 17.2.2.3 1,2,4-Triazines [Seite 424]
1.11.1.2.1 - 17.2.2.3.1 Monocyclic 1,2,4-Triazines [Seite 424]
1.11.1.2.1.1 - 17.2.2.3.1.1 Synthesis by Ring-Closure Reactions [Seite 424]
1.11.1.2.1.1.1 - 17.2.2.3.1.1.1 By Formation of Three N--C Bonds [Seite 424]
1.11.1.2.1.1.1.1 - 17.2.2.3.1.1.1.1 Fragments N--N--C, C--C, and N [Seite 424]
1.11.1.2.1.1.1.1.1 - 17.2.2.3.1.1.1.1.1 Method 1: Microwave-Assisted Reaction of a-Diazo-ß-oxo Esters with Hydrazides [Seite 424]
1.11.1.2.1.1.1.1.2 - 17.2.2.3.1.1.1.1.2 Method 2: Microwave-Assisted Condensation of 1,2-Dicarbonyl Compounds, Hydrazides, and Ammonium Acetate [Seite 425]
1.11.1.2.1.1.1.1.3 - 17.2.2.3.1.1.1.1.3 Method 3: Zirconium-Catalyzed Condensation of Benzil with Hydrazides [Seite 426]
1.11.1.2.1.1.1.2 - 17.2.2.3.1.1.1.2 Fragments N--N, C--C, C--N [Seite 427]
1.11.1.2.1.1.1.2.1 - 17.2.2.3.1.1.1.2.1 Method 1: One-Pot Condensation of Amides, 1,2-Diketones, and Hydrazine [Seite 427]
1.11.1.2.1.1.2 - 17.2.2.3.1.1.2 By Formation of Two N--C Bonds [Seite 430]
1.11.1.2.1.1.2.1 - 17.2.2.3.1.1.2.1 Fragments N--N--C--N and C--C [Seite 430]
1.11.1.2.1.1.2.1.1 - 17.2.2.3.1.1.2.1.1 Method 1: Reaction of 1,2-Dicarbonyl Compounds with Amidrazones [Seite 430]
1.11.1.2.1.1.2.1.2 - 17.2.2.3.1.1.2.1.2 Method 2: Reaction of 1,2-Dicarbonyl Compounds with Semicarbazides, Thiosemicarbazides, or Selenosemicarbazides [Seite 432]
1.11.1.2.1.1.2.1.3 - 17.2.2.3.1.1.2.1.3 Method 3: Cyclization of Hydrazonoimidazolidines with a-Oxo Esters [Seite 433]
1.11.1.2.1.1.2.1.4 - 17.2.2.3.1.1.2.1.4 Method 4: Reaction of Aminoguanidines with a,a-Dihalo Ketones [Seite 434]
1.11.1.2.1.1.2.1.5 - 17.2.2.3.1.1.2.1.5 Method 5: Condensation of Thiosemicarbazide with Dialkyl Acetylenedicarboxylates [Seite 436]
1.11.1.2.1.1.2.1.6 - 17.2.2.3.1.1.2.1.6 Method 6: Reaction of a-Functionalized Acetonitriles with 1H-Tetrazol-5-amine [Seite 437]
1.11.1.2.1.1.2.2 - 17.2.2.3.1.1.2.2 Fragments N--C--C--N--N and C [Seite 438]
1.11.1.2.1.1.2.2.1 - 17.2.2.3.1.1.2.2.1 Method 1: Condensation of Aryl(hydrazono)acetaldehyde Oximes with Pyridine-2,6-dicarbaldehyde [Seite 438]
1.11.1.2.1.1.2.2.2 - 17.2.2.3.1.1.2.2.2 Method 2: Condensation of Aryl(hydrazono)acetaldehyde Oximes with Pyridinecarbaldehydes [Seite 439]
1.11.1.2.1.1.2.2.3 - 17.2.2.3.1.1.2.2.3 Method 3: Condensation of Aryl(hydrazono)acetaldehyde Oximes with Quinoline-2-carbaldehydes [Seite 440]
1.11.1.2.1.1.3 - 17.2.2.3.1.1.3 By Formation of One N--C Bond [Seite 441]
1.11.1.2.1.1.3.1 - 17.2.2.3.1.1.3.1 Fragment C--C--N--N--C--N [Seite 441]
1.11.1.2.1.1.3.1.1 - 17.2.2.3.1.1.3.1.1 Method 1: Cyclization of Silyl-Substituted Thiosemicarbazone Acetic Acid Esters [Seite 441]
1.11.1.2.1.1.3.2 - 17.2.2.3.1.1.3.2 Fragment C--N--C--C--N--N [Seite 442]
1.11.1.2.1.1.3.2.1 - 17.2.2.3.1.1.3.2.1 Method 1: Cyclization of a,ß-Unsaturated a-Amido Hydrazides [Seite 442]
1.11.1.2.1.2 - 17.2.2.3.1.2 Annulation by the Formation of a Second Heterocyclic Ring [Seite 443]
1.11.1.2.1.2.1 - 17.2.2.3.1.2.1 Method 1: Cyclization of Hydrazides with 1,2,4-Triazin-3(2H)-ones [Seite 443]
1.11.1.2.1.2.2 - 17.2.2.3.1.2.2 Method 2: Cyclization of 6-Benzyl-5-hydrazino-1,2,4-triazin-3(2H)-one with Amidinium Salts [Seite 444]
1.11.1.2.1.2.3 - 17.2.2.3.1.2.3 Method 3: Sonagashira Coupling-Cyclization of 6-Chloro-1,2,4-triazine-3,5-diamines [Seite 445]
1.11.1.2.1.2.4 - 17.2.2.3.1.2.4 Method 4: Cyclization of 6-Acetamido-1,2,4-triazine-5-carboxylates [Seite 446]
1.11.1.2.1.2.5 - 17.2.2.3.1.2.5 Method 5: Cyclization of 3-Amino-1,2,4-triazin-5(4H)-ones with Glyoxal [Seite 447]
1.11.1.2.1.2.6 - 17.2.2.3.1.2.6 Method 6: Cyclization of 5-Azido-2,3-dimethyl-2H-pyrazolo[4,3-e][1,2,4]triazine [Seite 448]
1.11.1.2.1.2.7 - 17.2.2.3.1.2.7 Method 7: Cyclization of 5-[Hydrazono(3,4,5-trimethoxyphenyl)methyl]-1,2,4-triazin-6(1H)-ones [Seite 449]
1.11.1.2.1.3 - 17.2.2.3.1.3 Aromatization [Seite 450]
1.11.1.2.1.3.1 - 17.2.2.3.1.3.1 Method 1: Dehydration of Dihydrotriazines [Seite 450]
1.11.1.2.1.3.2 - 17.2.2.3.1.3.2 Method 2: N-Deacylation and Oxidation of Tetrahydro-1,2,4-triazine [Seite 450]
1.11.1.2.1.4 - 17.2.2.3.1.4 Synthesis by Substituent Modification [Seite 451]
1.11.1.2.1.4.1 - 17.2.2.3.1.4.1 Substitution of Existing Substituents [Seite 451]
1.11.1.2.1.4.1.1 - 17.2.2.3.1.4.1.1 Of Hydrogen [Seite 451]
1.11.1.2.1.4.1.1.1 - 17.2.2.3.1.4.1.1.1 Method 1: Reaction of 1,2,4-Triazine 4-Oxides with Terminal Alkynes [Seite 451]
1.11.1.2.1.4.1.2 - 17.2.2.3.1.4.1.2 Of Carbon Functionalities [Seite 452]
1.11.1.2.1.4.1.2.1 - 17.2.2.3.1.4.1.2.1 Method 1: Reaction of 1,2,4-Triazine-5-carbonitriles with Nucleophiles [Seite 452]
1.11.1.2.1.4.1.3 - 17.2.2.3.1.4.1.3 Of Heteroatoms [Seite 453]
1.11.1.2.1.4.1.3.1 - 17.2.2.3.1.4.1.3.1 Method 1: Reaction of Chloro-Substituted 1,2,4-Triazines with Amines [Seite 453]
1.11.1.2.1.4.1.3.2 - 17.2.2.3.1.4.1.3.2 Method 2: Reaction of Methylsulfonyl-Substituted 1,2,4-Triazines with Alkynyllithium Reagents [Seite 454]
1.11.1.2.1.4.1.3.3 - 17.2.2.3.1.4.1.3.3 Method 3: Reaction of Methylsulfanyl-Substituted 1,2,4-Triazines with Amines [Seite 455]
1.11.1.2.1.4.1.3.4 - 17.2.2.3.1.4.1.3.4 Method 4: Deamination with Preyssler's Anion [Seite 457]
1.11.1.2.1.4.2 - 17.2.2.3.1.4.2 Addition Reactions [Seite 458]
1.11.1.2.1.4.2.1 - 17.2.2.3.1.4.2.1 Method 1: Nucleophilic Addition of Cyanide to 1,2,4-Triazine 4-Oxides [Seite 458]
1.11.1.2.1.4.2.2 - 17.2.2.3.1.4.2.2 Method 2: Nucleophilic Addition of Indoles to 1,2,4-Triazine 4-Oxides [Seite 459]
1.11.1.2.1.4.2.3 - 17.2.2.3.1.4.2.3 Method 3: Nucleophilic Addition of Carboranes to 1,2,4-Triazine 4-Oxides [Seite 460]
1.11.1.2.1.4.3 - 17.2.2.3.1.4.3 Modification of Substituents [Seite 461]
1.11.1.2.1.4.3.1 - 17.2.2.3.1.4.3.1 Method 1: Methylation of 3-Thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-ones [Seite 461]
1.11.1.2.1.4.3.2 - 17.2.2.3.1.4.3.2 Method 2: N-Acylation of Ethyl 6-Amino-1,2,4-triazine-5-carboxylate [Seite 461]
1.11.1.2.1.4.3.3 - 17.2.2.3.1.4.3.3 Method 3: Displacement of an a-Hydroxy Group with a Halide [Seite 462]
1.11.1.2.1.4.3.4 - 17.2.2.3.1.4.3.4 Method 4: a-Halogen Exchange [Seite 462]
1.11.1.2.1.4.3.5 - 17.2.2.3.1.4.3.5 Method 5: Displacement of an a-Fluoride with Amines [Seite 463]
1.11.1.2.1.4.3.6 - 17.2.2.3.1.4.3.6 Method 6: Displacement of an a-Chloride with Thiols [Seite 463]
1.11.1.2.1.4.3.7 - 17.2.2.3.1.4.3.7 Method 7: Displacement of an a-Chloride with Amines [Seite 464]
1.11.1.2.1.4.3.8 - 17.2.2.3.1.4.3.8 Method 8: Displacement of an a-Chloride by Wittig Reaction [Seite 465]
1.11.1.2.1.4.3.9 - 17.2.2.3.1.4.3.9 Method 9: Ring Cleavage of Tetrazolo[1,5-b][1,2,4]triazin-7-amines [Seite 467]
1.11.1.2.1.4.3.10 - 17.2.2.3.1.4.3.10 Method 10: Palladium-Catalyzed Arylation of 1,2,4-Triazin-3-amine [Seite 468]
1.11.1.2.2 - 17.2.2.3.2 1,2,4-Benzotriazines and Related Compounds [Seite 469]
1.11.1.2.2.1 - 17.2.2.3.2.1 Synthesis by Ring-Closure Reactions [Seite 469]
1.11.1.2.2.1.1 - 17.2.2.3.2.1.1 By Formation of One N--N and One N--C Bond [Seite 469]
1.11.1.2.2.1.1.1 - 17.2.2.3.2.1.1.1 Fragments N--C--C--N and N--C [Seite 469]
1.11.1.2.2.1.1.1.1 - 17.2.2.3.2.1.1.1.1 Method 1: Reaction of 2-Nitroanilines with Cyanamide [Seite 469]
1.11.1.2.2.1.1.2 - 17.2.2.3.2.1.1.2 Fragments N--C--N and N--C--C [Seite 470]
1.11.1.2.2.1.1.2.1 - 17.2.2.3.2.1.1.2.1 Method 1: Reaction of 1-Halo-2-nitrobenzenes with Guanidine Hydrochloride [Seite 470]
1.11.1.2.2.2 - 17.2.2.3.2.2 Synthesis by Ring Transformation [Seite 470]
1.11.1.2.2.2.1 - 17.2.2.3.2.2.1 Method 1: Isomerization of Angular Triazinium Salts [Seite 470]
1.11.1.2.2.3 - 17.2.2.3.2.3 Synthesis by Substituent Modification [Seite 471]
1.11.1.2.2.3.1 - 17.2.2.3.2.3.1 Addition Reactions [Seite 471]
1.11.1.2.2.3.1.1 - 17.2.2.3.2.3.1.1 Method 1: Oxidation of 1,2,4-Benzotriazin-3-amine 1-Oxides [Seite 471]
1.11.1.3 - 17.2.3.6 1,3,5-Triazines and Phosphorus Analogues [Seite 474]
1.11.1.3.1 - 17.2.3.6.1 1,3,5-Triazines [Seite 474]
1.11.1.3.1.1 - 17.2.3.6.1.1 Synthesis by Ring-Closure Reactions [Seite 474]
1.11.1.3.1.1.1 - 17.2.3.6.1.1.1 By Formation of Three N--C Bonds [Seite 474]
1.11.1.3.1.1.1.1 - 17.2.3.6.1.1.1.1 Fragments N--C, N--C, and N--C [Seite 474]
1.11.1.3.1.1.1.1.1 - 17.2.3.6.1.1.1.1.1 Method 1: Trimerization of Dialkylcyanamides or Nitriles [Seite 474]
1.11.1.3.1.1.1.1.2 - 17.2.3.6.1.1.1.1.2 Method 2: Trimerization of Imidates [Seite 475]
1.11.1.3.1.1.1.1.3 - 17.2.3.6.1.1.1.1.3 Method 3: Reaction of Carbodiimides with Nitrilium Salts [Seite 476]
1.11.1.3.1.1.2 - 17.2.3.6.1.1.2 By Formation of Two N--C Bonds [Seite 477]
1.11.1.3.1.1.2.1 - 17.2.3.6.1.1.2.1 Fragments N--C--N--C and N--C [Seite 477]
1.11.1.3.1.1.2.1.1 - 17.2.3.6.1.1.2.1.1 Method 1: Reaction of Guanidine-1-carbonitrile with Nitriles [Seite 477]
1.11.1.3.1.1.2.2 - 17.2.3.6.1.1.2.2 Fragments N--C--N and C--N--C [Seite 479]
1.11.1.3.1.1.2.2.1 - 17.2.3.6.1.1.2.2.1 Method 1: Reaction of Isothiocyanates with Amidines or Guanidines [Seite 479]
1.11.1.3.1.1.2.2.2 - 17.2.3.6.1.1.2.2.2 Method 2: Reaction of Isothiocyanates with Sodium Hydrogen Cyanamide [Seite 480]
1.11.1.3.1.1.2.2.3 - 17.2.3.6.1.1.2.2.3 Method 3: Reaction of N-Functionalized Imidoyl Chlorides with Amidine Derivatives [Seite 481]
1.11.1.3.1.1.2.2.4 - 17.2.3.6.1.1.2.2.4 Method 4: Reaction of N-(2,2-Dichlorovinyl)benzamides with Amidines [Seite 484]
1.11.1.3.1.1.2.2.5 - 17.2.3.6.1.1.2.2.5 Method 5: Reaction of 4-Oxo-1,3-benzoxazinium Perchlorates with Guanidines [Seite 485]
1.11.1.3.1.1.2.2.6 - 17.2.3.6.1.1.2.2.6 Method 6: Reaction of Amidinium Salts with Pyrazolamines or 1,2,4-Triazolamines [Seite 486]
1.11.1.3.1.1.2.3 - 17.2.3.6.1.1.2.3 Fragments N--C--N--C--N and C [Seite 487]
1.11.1.3.1.1.2.3.1 - 17.2.3.6.1.1.2.3.1 Method 1: Reaction of Biguanides with Carboxylic Acid Derivatives [Seite 487]
1.11.1.3.1.1.2.3.2 - 17.2.3.6.1.1.2.3.2 Method 2: Reaction of Zinc(II) Bis[bis(methoxyimido)amide] with Carboxylic Acid Derivatives [Seite 490]
1.11.1.3.1.2 - 17.2.3.6.1.2 Synthesis by Substituent Modification [Seite 491]
1.11.1.3.1.2.1 - 17.2.3.6.1.2.1 Substitution of Existing Substituents [Seite 491]
1.11.1.3.1.2.1.1 - 17.2.3.6.1.2.1.1 Of Hydrogen [Seite 491]
1.11.1.3.1.2.1.1.1 - 17.2.3.6.1.2.1.1.1 Method 1: Amination [Seite 491]
1.11.1.3.1.2.1.2 - 17.2.3.6.1.2.1.2 Of Carbon Functionalities [Seite 492]
1.11.1.3.1.2.1.2.1 - 17.2.3.6.1.2.1.2.1 Method 1: Substitution of Trinitromethyl Groups [Seite 492]
1.11.1.3.1.2.1.2.2 - 17.2.3.6.1.2.1.2.2 Method 2: Substitution of Cyano Groups [Seite 493]
1.11.1.3.1.2.1.2.3 - 17.2.3.6.1.2.1.2.3 Method 3: Substitution of Bis(tert-Butoxycarbonyl)(nitro)methyl Groups [Seite 495]
1.11.1.3.1.2.1.3 - 17.2.3.6.1.2.1.3 Of Halogens by Carbon Functionalities [Seite 495]
1.11.1.3.1.2.1.3.1 - 17.2.3.6.1.2.1.3.1 Method 1: Reaction with Grignard Reagents [Seite 495]
1.11.1.3.1.2.1.3.2 - 17.2.3.6.1.2.1.3.2 Method 2: Reaction with Boronic Acids (Suzuki Coupling) [Seite 498]
1.11.1.3.1.2.1.3.3 - 17.2.3.6.1.2.1.3.3 Method 3: Reaction with Organotin Reagents [Seite 499]
1.11.1.3.1.2.1.3.4 - 17.2.3.6.1.2.1.3.4 Method 4: Reaction with Arynes [Seite 500]
1.11.1.3.1.2.1.3.5 - 17.2.3.6.1.2.1.3.5 Method 5: Reaction with Arylzinc Chlorides (Negishi Coupling) [Seite 502]
1.11.1.3.1.2.1.3.6 - 17.2.3.6.1.2.1.3.6 Method 6: Nickel-Catalyzed Ullmann Homocoupling Reactions [Seite 502]
1.11.1.3.1.2.1.3.7 - 17.2.3.6.1.2.1.3.7 Method 7: Cobalt-Catalyzed Arylation or Benzylation Reactions [Seite 503]
1.11.1.3.1.2.1.3.8 - 17.2.3.6.1.2.1.3.8 Method 8: Sonagashira Reactions [Seite 505]
1.11.1.3.1.2.1.3.9 - 17.2.3.6.1.2.1.3.9 Method 9: Cross-Coupling Reactions with Organoaluminum Compounds [Seite 505]
1.11.1.3.1.2.1.4 - 17.2.3.6.1.2.1.4 Of Halogens by Oxygen Functionalities [Seite 506]
1.11.1.3.1.2.1.4.1 - 17.2.3.6.1.2.1.4.1 Method 1: Exchange of Chlorine in 2,4,6-Trichloro-1,3,5-triazine [Seite 506]
1.11.1.3.1.2.1.4.2 - 17.2.3.6.1.2.1.4.2 Method 2: Exchange of Chlorine in Chloro-Substituted 1,3,5-Triazines [Seite 509]
1.11.1.3.1.2.1.5 - 17.2.3.6.1.2.1.5 Of Halogens by Sulfur Functionalities [Seite 509]
1.11.1.3.1.2.1.5.1 - 17.2.3.6.1.2.1.5.1 Method 1: Exchange of Chlorine for an Alkylsulfanyl Group [Seite 509]
1.11.1.3.1.2.1.5.2 - 17.2.3.6.1.2.1.5.2 Method 2: Exchange of Chlorine for an Arylsulfanyl Group [Seite 509]
1.11.1.3.1.2.1.6 - 17.2.3.6.1.2.1.6 Substitution of Halogens by Selenium or Tellurium Functionalities [Seite 510]
1.11.1.3.1.2.1.6.1 - 17.2.3.6.1.2.1.6.1 Method 1: Exchange of Chlorine with Chalcogenide Nucleophiles [Seite 510]
1.11.1.3.1.2.1.7 - 17.2.3.6.1.2.1.7 Of Halogens by Nitrogen Functionalities [Seite 510]
1.11.1.3.1.2.1.7.1 - 17.2.3.6.1.2.1.7.1 Method 1: Reaction of 2,4,6-Trichloro-1,3,5-triazine with Amines (Monosubstitution) [Seite 510]
1.11.1.3.1.2.1.7.2 - 17.2.3.6.1.2.1.7.2 Method 2: Reaction of 2,4,6-Trichloro-1,3,5-triazine with Amines (Trisubstitution) [Seite 511]
1.11.1.3.1.2.1.7.3 - 17.2.3.6.1.2.1.7.3 Method 3: Reaction of 2,4-Dichloro-1,3,5-triazines with Amines [Seite 513]
1.11.1.3.1.2.1.7.4 - 17.2.3.6.1.2.1.7.4 Method 4: Reaction of 2-Chloro-1,3,5-triazines with Amines [Seite 514]
1.11.1.3.1.2.1.7.5 - 17.2.3.6.1.2.1.7.5 Method 5: Reaction of 2-Chloro-1,3,5-triazines with Ureas or Thioureas [Seite 515]
1.11.1.3.1.2.1.8 - 17.2.3.6.1.2.1.8 Generation of 1,3,5-Triazine Libraries by Substitution of Chlorine by Oxygen or Nitrogen Functionalities [Seite 517]
1.11.1.3.1.2.1.8.1 - 17.2.3.6.1.2.1.8.1 Method 1: Parallel Synthesis on Solid Supports [Seite 517]
1.11.1.3.1.2.1.9 - 17.2.3.6.1.2.1.9 Of Sulfur Functionalities [Seite 518]
1.11.1.3.1.2.1.9.1 - 17.2.3.6.1.2.1.9.1 Method 1: Substitution of Sulfonyl Groups [Seite 518]
1.11.1.3.1.2.1.9.2 - 17.2.3.6.1.2.1.9.2 Method 2: Cross Coupling of Sulfanyl-Substituted 1,3,5-Triazines with Functionalized Organozinc Reagents [Seite 518]
1.11.1.3.1.2.1.9.3 - 17.2.3.6.1.2.1.9.3 Method 3: Reductive Rearrangement of 2-(Triazinylsulfanyl)benzamides [Seite 519]
1.11.1.3.1.2.2 - 17.2.3.6.1.2.2 Rearrangement of Substituents [Seite 520]
1.11.1.3.1.2.2.1 - 17.2.3.6.1.2.2.1 Method 1: Smiles Rearrangement [Seite 520]
1.11.1.3.1.2.2.2 - 17.2.3.6.1.2.2.2 Method 2: Thermal Isomerization of 2,4,6-Trialkoxy-1,3,5-triazines [Seite 521]
1.11.1.3.1.2.3 - 17.2.3.6.1.2.3 Modification of Substituents [Seite 521]
1.11.1.3.1.2.3.1 - 17.2.3.6.1.2.3.1 Method 1: S-Oxidation [Seite 521]
1.11.1.3.1.2.3.2 - 17.2.3.6.1.2.3.2 Method 2: Modification at the a-Carbon [Seite 521]
1.11.1.3.1.2.3.2.1 - 17.2.3.6.1.2.3.2.1 Variation 1: Conversion of Trinitromethyl Groups into Nitriles [Seite 521]
1.11.1.3.1.2.3.2.2 - 17.2.3.6.1.2.3.2.2 Variation 2: Conversion of Trinitromethyl Groups into Nitrile Oxides and Subsequent Heterocycle Formation [Seite 522]
1.11.1.3.1.2.3.2.3 - 17.2.3.6.1.2.3.2.3 Variation 3: Conversion of Dinitromethyl Groups into Oxadiazole 2-Oxides [Seite 525]
1.11.1.3.1.2.3.2.4 - 17.2.3.6.1.2.3.2.4 Variation 4: Conversion of Alkynyltriazines into Triazoles Using Click Chemistry [Seite 525]
1.11.1.3.1.2.3.3 - 17.2.3.6.1.2.3.3 Method 3: Reaction of Nitrogen Substituents [Seite 526]
1.11.1.3.1.2.3.3.1 - 17.2.3.6.1.2.3.3.1 Variation 1: N-Heterocycle Formation [Seite 526]
1.11.1.3.1.2.3.3.2 - 17.2.3.6.1.2.3.3.2 Variation 2: N-Alkylation [Seite 527]
1.11.1.3.1.2.3.3.3 - 17.2.3.6.1.2.3.3.3 Variation 3: Debenzylation [Seite 528]
1.11.1.3.1.2.3.3.4 - 17.2.3.6.1.2.3.3.4 Variation 4: Thiourea and Thiazole Formation [Seite 528]
1.12 - Volume 34: Fluorine [Seite 532]
1.12.1 - 34.1 Product Class 1: Fluoroalkanes [Seite 532]
1.12.1.1 - 34.1.1.7 Synthesis by Substitution of Hydrogen [Seite 532]
1.12.1.1.1 - 34.1.1.7.1 Method 1: Direct Fluorination with Elemental Fluorine [Seite 533]
1.12.1.1.2 - 34.1.1.7.2 Method 2: Reaction with Selectfluor [Seite 535]
1.13 - Author Index [Seite 540]
1.14 - Abbreviations [Seite 560]
1.15 - List of All Volumes [Seite 566]