1 - Science of Synthesis: Knowledge Updates 2018/2 [Seite 1]
2 - Title Page [Seite 7]
3 - Copyright [Seite 8]
4 - Preface [Seite 9]
5 - Abstracts [Seite 11]
6 - Overview [Seite 13]
7 - Table of Contents [Seite 15]
8 - 10.23 Product Class 23: Pyrido[X,Y-b]indoles (Carbolines) [Seite 33]
8.1 - 10.23.1 Product Subclass 1: 9H-Pyrido[2,3-b]indoles (?-Carbolines) [Seite 38]
8.1.1 - 10.23.1.1 Synthesis by Ring-Closure Reactions [Seite 38]
8.1.1.1 - 10.23.1.1.1 By Annulation to an Arene [Seite 38]
8.1.1.1.1 - 10.23.1.1.1.1 By Formation of Four N-C and Two C-C Bonds [Seite 38]
8.1.1.1.1.1 - 10.23.1.1.1.1.1 With Formation of 1-2, 2-3, 4-4a, 1-9a, 8a-9, and 9-9a Bonds [Seite 38]
8.1.1.1.1.1.1 - 10.23.1.1.1.1.1.1 Method 1: From 1-Bromo-2-(2,2-dibromovinyl)benzenes, Ammonia, and Alkyl Aldehydes [Seite 38]
8.1.1.1.2 - 10.23.1.1.1.2 By Formation of Two N-C and One C-C Bonds [Seite 40]
8.1.1.1.2.1 - 10.23.1.1.1.2.1 With Formation of 1-9a, 4-4a, and 9-9a Bonds [Seite 40]
8.1.1.1.2.1.1 - 10.23.1.1.1.2.1.1 Method 1: From (2-Nitroaryl)acetonitriles and 3-Acetoxy-3-aryl-2-methylene Ketones [Seite 40]
8.1.1.1.2.1.2 - 10.23.1.1.1.2.1.2 Method 2: From (2-Nitrophenyl)acetonitrile and 3-Arylenones [Seite 42]
8.1.1.1.2.1.2.1 - 10.23.1.1.1.2.1.2.1 Variation 1: From (2-Nitrophenyl)acetonitrile and 4H-1-Benzopyran-4-ones [Seite 44]
8.1.1.1.3 - 10.23.1.1.1.3 By Formation of Two N-C Bonds [Seite 45]
8.1.1.1.3.1 - 10.23.1.1.1.3.1 With Formation of 8a-9 and 9-9a Bonds [Seite 45]
8.1.1.1.3.1.1 - 10.23.1.1.1.3.1.1 Method 1: From Primary Amines and 3-(2-Bromophenyl)-2-chloropyridine [Seite 45]
8.1.1.1.4 - 10.23.1.1.1.4 By Formation of One N-C Bond and One C-C Bond [Seite 47]
8.1.1.1.4.1 - 10.23.1.1.1.4.1 With Formation of 4a-4b and 9-9a Bonds [Seite 47]
8.1.1.1.4.1.1 - 10.23.1.1.1.4.1.1 Method 1: From 2,3-Dihalopyridines and Anilines [Seite 47]
8.1.1.1.4.1.2 - 10.23.1.1.1.4.1.2 Method 2: From 2-Iodopyridine and a 2-Bromoaniline [Seite 48]
8.1.1.1.5 - 10.23.1.1.1.5 By Formation of Two C-C Bonds [Seite 49]
8.1.1.1.5.1 - 10.23.1.1.1.5.1 With Formation of 3-4 and 4a-9a Bonds [Seite 49]
8.1.1.1.5.1.1 - 10.23.1.1.1.5.1.1 Method 1: From (2-Alkenylaryl)carbodiimides [Seite 49]
8.1.1.1.5.1.2 - 10.23.1.1.1.5.1.2 Method 2: From N-Acyl-N-(2-alkynylaryl)pyrimidin-2-amines or 3-[(2-Alkynylphenyl)amino]pyrazin-2-ones [Seite 51]
8.1.1.1.6 - 10.23.1.1.1.6 By Formation of One N-C Bond [Seite 53]
8.1.1.1.6.1 - 10.23.1.1.1.6.1 With Formation of the 9-9a Bond [Seite 53]
8.1.1.1.6.1.1 - 10.23.1.1.1.6.1.1 Method 1: From 3-(2-Azidoaryl)pyridines [Seite 53]
8.1.1.1.6.1.1.1 - 10.23.1.1.1.6.1.1.1 Variation 1: From 3-(2-Azidoaryl)pyridinium Trifluoromethanesulfonates and a Rhodium Catalyst [Seite 54]
8.1.1.1.6.1.2 - 10.23.1.1.1.6.1.2 Method 2: From 3-(2-Nitroaryl)pyridines [Seite 55]
8.1.1.1.6.1.2.1 - 10.23.1.1.1.6.1.2.1 Variation 1: From 3-(2-Nitrosoaryl)pyridines [Seite 56]
8.1.1.1.6.1.3 - 10.23.1.1.1.6.1.3 Method 3: From 2-(3-Pyridyl)-N-tosylanilines or N-Acetyl-2-(3-pyridyl)-anilines [Seite 56]
8.1.1.1.6.1.4 - 10.23.1.1.1.6.1.4 Method 4: From N-[2-(2-Fluoropyridin-3-yl)phenyl]pivalamide [Seite 58]
8.1.1.1.7 - 10.23.1.1.1.7 By Formation of One C-C Bond [Seite 58]
8.1.1.1.7.1 - 10.23.1.1.1.7.1 With Formation of the 4a-4b Bond [Seite 58]
8.1.1.1.7.1.1 - 10.23.1.1.1.7.1.1 Method 1: From N-Arylpyridin-2-amines [Seite 58]
8.1.1.1.7.1.1.1 - 10.23.1.1.1.7.1.1.1 Variation 1: From N,N-Diphenylpyridin-2-amine or N-Methyl-N-phenylpyridin-2-amine [Seite 59]
8.1.1.1.7.1.2 - 10.23.1.1.1.7.1.2 Method 2: From N2-Phenylpyridine-2,3-diamines [Seite 60]
8.1.1.1.7.1.3 - 10.23.1.1.1.7.1.3 Method 3: From an N-Arylpyridin-2-amine with at Least One Halogen on at Least One Ring [Seite 61]
8.1.1.1.7.1.3.1 - 10.23.1.1.1.7.1.3.1 Variation 1: From N-Aryl-3-chloropyridin-2-amines by Palladium Catalysis [Seite 61]
8.1.1.1.7.1.3.2 - 10.23.1.1.1.7.1.3.2 Variation 2: From N-Aryl-3-bromopyridin-2-amines with Palladium Catalysis [Seite 62]
8.1.1.1.7.1.3.3 - 10.23.1.1.1.7.1.3.3 Variation 3: From N-[3-Chloro-1-methylpyridin-2(1H)-ylidene]anilines [Seite 65]
8.1.1.1.7.1.3.4 - 10.23.1.1.1.7.1.3.4 Variation 4: From N-(Chloroaryl)-3-chloro-1-methylpyridin-2(1H)-imines and Secondary Amines [Seite 66]
8.1.1.1.7.1.3.5 - 10.23.1.1.1.7.1.3.5 Variation 5: From N-Aryl-3-halopyridin-2-amines by Photostimulated SRN1 Reactions [Seite 69]
8.1.1.1.7.1.3.6 - 10.23.1.1.1.7.1.3.6 Variation 6: From 3-Bromo-N-(2-bromophenyl)pyridin-2-amines by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates [Seite 71]
8.1.1.2 - 10.23.1.1.2 By Annulation to a Heterocycle [Seite 71]
8.1.1.2.1 - 10.23.1.1.2.1 By Annulation to a Pyridine [Seite 71]
8.1.1.2.1.1 - 10.23.1.1.2.1.1 By Formation of One N-C and One C-C Bond [Seite 71]
8.1.1.2.1.1.1 - 10.23.1.1.2.1.1.1 With Formation of 4a-4b and 8a-9 Bonds [Seite 71]
8.1.1.2.1.1.1.1 - 10.23.1.1.2.1.1.1.1 Method 1: From Pyridin-2,4,6-triamine [Seite 71]
8.1.1.2.2 - 10.23.1.1.2.2 By Annulation to an Indole [Seite 72]
8.1.1.2.2.1 - 10.23.1.1.2.2.1 By Formation of Two N-C and One C-C Bonds [Seite 72]
8.1.1.2.2.1.1 - 10.23.1.1.2.2.1.1 With Formation of 1-2, 1-9a, and 4-4a Bonds [Seite 72]
8.1.1.2.2.1.1.1 - 10.23.1.1.2.2.1.1.1 Method 1: From 2-Bromo-1H-indole [Seite 72]
8.1.1.2.2.2 - 10.23.1.1.2.2.2 By Formation of One N-C and Two C-C Bonds [Seite 73]
8.1.1.2.2.2.1 - 10.23.1.1.2.2.2.1 With Formation of 1-2, 2-3, and 4-4a Bonds [Seite 73]
8.1.1.2.2.2.1.1 - 10.23.1.1.2.2.2.1.1 Method 1: From Ethyl 2-Amino-1H-indole-3-carboxylates, an Arylacetylene, and an Aryl Aldehyde [Seite 73]
8.1.1.2.2.3 - 10.23.1.1.2.2.3 By Formation of Two N-C Bonds [Seite 75]
8.1.1.2.2.3.1 - 10.23.1.1.2.2.3.1 With Formation of 1-2 and 1-9a Bonds [Seite 75]
8.1.1.2.2.3.1.1 - 10.23.1.1.2.2.3.1.1 Method 1: From 1,5-Dicarbonyl Compounds or Equivalents [Seite 75]
8.1.1.2.2.4 - 10.23.1.1.2.2.4 By Formation of One N-C and One C-C Bonds [Seite 78]
8.1.1.2.2.4.1 - 10.23.1.1.2.2.4.1 With Formation of 1-2 and 4-4a Bonds [Seite 78]
8.1.1.2.2.4.1.1 - 10.23.1.1.2.2.4.1.1 Method 1: From 1H-Indol-2-amines and Alkynones [Seite 78]
8.1.1.2.2.4.1.1.1 - 10.23.1.1.2.2.4.1.1.1 Variation 1: From 1H-Indol-2-amines and 1,3-Diketones [Seite 80]
8.1.1.2.2.4.1.1.2 - 10.23.1.1.2.2.4.1.1.2 Variation 2: From N-(Phosphoranylidene)indol-2-amines [Seite 81]
8.1.1.2.2.4.1.2 - 10.23.1.1.2.2.4.1.2 Method 2: From N-(Arylsulfonyl)-3-diazo-1,3-dihydroindol-2-imines [Seite 82]
8.1.1.2.2.4.2 - 10.23.1.1.2.2.4.2 With Formation of 1-2 and 2-3 Bonds [Seite 84]
8.1.1.2.2.4.2.1 - 10.23.1.1.2.2.4.2.1 Method 1: From 3-Alkenyl-N-(triphenylphosphoranylidene)-1H-indol-2-amines [Seite 84]
8.1.1.2.2.4.2.1.1 - 10.23.1.1.2.2.4.2.1.1 Variation 1: From 3-(2-Nitrovinyl)-N-(triphenylphosphoranylidene)-1H-indol-2-amines [Seite 85]
8.1.1.2.2.4.3 - 10.23.1.1.2.2.4.3 With Formation of 1-2 and 3-4 Bonds [Seite 86]
8.1.1.2.2.4.3.1 - 10.23.1.1.2.2.4.3.1 Method 1: From a 2-Amino-1H-indole-3-carbothioaldehyde [Seite 86]
8.1.1.2.2.4.4 - 10.23.1.1.2.2.4.4 With Formation of 1-9a and 3-4 Bonds [Seite 87]
8.1.1.2.2.4.4.1 - 10.23.1.1.2.2.4.4.1 Method 1: From 3-[Bis(methylsulfanyl)methylene]-1-methyl-1,3-dihydro-2H-indol-2-one [Seite 87]
8.1.1.2.2.5 - 10.23.1.1.2.2.5 By Formation of Two C-C Bonds [Seite 88]
8.1.1.2.2.5.1 - 10.23.1.1.2.2.5.1 With Formation of 3-4 and 4-4a Bonds [Seite 88]
8.1.1.2.2.5.1.1 - 10.23.1.1.2.2.5.1.1 Method 1: From N-(1H-Indol-2-yl)acetamide [Seite 88]
8.1.1.2.2.6 - 10.23.1.1.2.2.6 By Formation of One N-C Bond [Seite 88]
8.1.1.2.2.6.1 - 10.23.1.1.2.2.6.1 With Formation of the 1-9b Bond [Seite 88]
8.1.1.2.2.6.1.1 - 10.23.1.1.2.2.6.1.1 Method 1: From 3-(1H-Indol-3-yl)allyl Azides [Seite 88]
8.1.1.2.2.6.1.2 - 10.23.1.1.2.2.6.1.2 Method 2: From 3-(1H-Indol-3-yl)propanone O-2,4-Dinitrophenyl Oximes [Seite 89]
8.1.1.2.2.6.1.2.1 - 10.23.1.1.2.2.6.1.2.1 Variation 1: From 3-(1H-Indol-3-yl)propanone O-Pentafluorobenzoyl Oximes [Seite 90]
8.1.1.2.2.6.1.2.2 - 10.23.1.1.2.2.6.1.2.2 Variation 2: From 3-(1H-Indol-3-yl)propanone O-Acetyl Oximes [Seite 91]
8.1.1.2.2.6.1.2.3 - 10.23.1.1.2.2.6.1.2.3 Variation 3: From 3-(1H-Indol-3-yl)prop-2-enone O-Methyl Oximes [Seite 92]
8.1.1.2.2.6.1.3 - 10.23.1.1.2.2.6.1.3 Method 3: From a 3-(2-Bromo-1H-indol-3-yl)allylamine [Seite 93]
8.1.1.2.2.6.2 - 10.23.1.1.2.2.6.2 With Formation of the 1-2 Bond [Seite 94]
8.1.1.2.2.6.2.1 - 10.23.1.1.2.2.6.2.1 Method 1: From a 3-Propargyl-1H-indol-2-amine [Seite 94]
8.1.1.2.2.6.2.2 - 10.23.1.1.2.2.6.2.2 Method 2: From a 3-(2-Amino-1H-indol-3-yl)-2-cyanoacrylate [Seite 96]
8.1.1.2.2.6.2.3 - 10.23.1.1.2.2.6.2.3 Method 3: From N'-[3-(2-Aroylvinyl)-1H-indol-2-yl]alkanimidamides [Seite 97]
8.1.1.2.2.7 - 10.23.1.1.2.2.7 By Formation of One C-C Bond [Seite 98]
8.1.1.2.2.7.1 - 10.23.1.1.2.2.7.1 With Formation of the 2-3 Bond [Seite 98]
8.1.1.2.2.7.1.1 - 10.23.1.1.2.2.7.1.1 Method 1: From 3-Acetyl-2-(acylamino)-1H-indoles with Phosphoryl Chloride [Seite 98]
8.1.1.2.2.7.1.1.1 - 10.23.1.1.2.2.7.1.1.1 Variation 1: From 3-Acetyl-2-(acylamino)-1H-indoles with Potassium tert-Butoxide [Seite 100]
8.1.1.2.2.7.1.1.2 - 10.23.1.1.2.2.7.1.1.2 Variation 2: From N'-[3-(2-Aroylvinyl)-1H-indol-2-yl]alkanimidamides [Seite 101]
8.1.1.2.2.7.2 - 10.23.1.1.2.2.7.2 With Formation of the 3-4 Bond [Seite 102]
8.1.1.2.2.7.2.1 - 10.23.1.1.2.2.7.2.1 Method 1: From N'-(3-Cyano-1H-indol-2-yl)acetimidamides [Seite 102]
8.1.1.2.2.7.2.2 - 10.23.1.1.2.2.7.2.2 Method 2: From N'-(3-Formyl-1H-indol-2-yl)alkanimidamides [Seite 103]
8.1.1.2.2.7.2.3 - 10.23.1.1.2.2.7.2.3 Method 3: From a 2-Amino-1H-indole-3-carboxylate and a 1,3-Oxo Ester Equivalent [Seite 104]
8.1.1.2.3 - 10.23.1.1.2.3 By Annulation to a 1H-Pyrrolo[2,3-b]pyridine (a 7-Azaindole) [Seite 105]
8.1.1.2.3.1 - 10.23.1.1.2.3.1 By Formation of Three C-C Bonds [Seite 105]
8.1.1.2.3.1.1 - 10.23.1.1.2.3.1.1 With Formation of 4b-5, 6-7, and 8-8a Bonds [Seite 105]
8.1.1.2.3.1.1.1 - 10.23.1.1.2.3.1.1.1 Method 1: From a 1H-Pyrrolo[2,3-b]pyridine and Two Equivalents of Methyl Acrylate [Seite 105]
8.1.1.2.3.2 - 10.23.1.1.2.3.2 By Formation of Two C-C Bonds [Seite 106]
8.1.1.2.3.2.1 - 10.23.1.1.2.3.2.1 With Formation of 4b-5 and 8-8a Bonds [Seite 106]
8.1.1.2.3.2.1.1 - 10.23.1.1.2.3.2.1.1 Method 1: From a 1H-Pyrrolo[2,3-b]pyridine-3-boronic Acid [Seite 106]
8.1.1.2.3.2.2 - 10.23.1.1.2.3.2.2 With Formation of 4b-5 and 6-7 Bonds [Seite 106]
8.1.1.2.3.2.2.1 - 10.23.1.1.2.3.2.2.1 Method 1: From a 2-Vinyl-1H-pyrrolo[2,3-b]pyridine [Seite 106]
8.1.1.2.3.2.3 - 10.23.1.1.2.3.2.3 With Formation of 6-7 and 8-8b Bonds [Seite 108]
8.1.1.2.3.2.3.1 - 10.23.1.1.2.3.2.3.1 Method 1: From a 3-Vinyl-1H-pyrrolo[2,3-b]pyridine [Seite 108]
8.1.1.2.3.3 - 10.23.1.1.2.3.3 By Formation of One C-C Bond [Seite 108]
8.1.1.2.3.3.1 - 10.23.1.1.2.3.3.1 With Formation of the 8-8a Bond [Seite 108]
8.1.1.2.3.3.1.1 - 10.23.1.1.2.3.3.1.1 Method 1: Intramolecular Acylation [Seite 108]
8.1.2 - 10.23.1.2 Synthesis by Ring Transformation [Seite 109]
8.1.2.1 - 10.23.1.2.1 Method 1: From 1-(2-Pyridyl)-1H-benzotriazoles [Seite 109]
8.1.2.2 - 10.23.1.2.2 Method 2: From 3-Aryl-3H-[1,2,3]-triazolo[4,5-b]pyridines [Seite 110]
8.1.3 - 10.23.1.3 Aromatization [Seite 111]
8.1.4 - 10.23.1.4 Synthesis by Substituent Modification [Seite 114]
8.1.4.1 - 10.23.1.4.1 Substitution of Existing Substituents [Seite 114]
8.1.4.1.1 - 10.23.1.4.1.1 Substitution of N-Hydrogen [Seite 114]
8.1.4.1.1.1 - 10.23.1.4.1.1.1 Giving N-Sulfur 9H-Pyrido[2,3-b]indoles [Seite 114]
8.1.4.1.1.2 - 10.23.1.4.1.1.2 Giving N-Carbon 9H-Pyrido[2,3-b]indoles [Seite 115]
8.1.4.1.1.2.1 - 10.23.1.4.1.1.2.1 Method 1: Using an Alkyl or Aryl Halide [Seite 115]
8.1.4.1.1.2.2 - 10.23.1.4.1.1.2.2 Method 2: Via 1-Alkyl-9H-pyrido[2,3-b]indol-1-ium Salts [Seite 118]
8.1.4.1.1.2.3 - 10.23.1.4.1.1.2.3 Method 3: Using Acyl Halides or Anhydrides [Seite 119]
8.1.4.1.2 - 10.23.1.4.1.2 Substitution of N-Carbon and N-Sulfur [Seite 120]
8.1.4.1.2.1 - 10.23.1.4.1.2.1 Giving N-Hydrogen 9H-Pyrido[2,3-b]indoles [Seite 120]
8.1.4.1.2.1.1 - 10.23.1.4.1.2.1.1 Method 1: N-Deprotection [Seite 120]
8.1.4.1.3 - 10.23.1.4.1.3 Substitution of C-Hydrogen [Seite 121]
8.1.4.1.3.1 - 10.23.1.4.1.3.1 Direct Substitution by Electrophiles [Seite 121]
8.1.4.1.3.1.1 - 10.23.1.4.1.3.1.1 Method 1: Giving C-Halogen 9H-Pyrido[2,3-b]indoles [Seite 121]
8.1.4.1.3.1.2 - 10.23.1.4.1.3.1.2 Method 2: Giving C-Sulfur 9H-Pyrido[2,3-b]indoles [Seite 122]
8.1.4.1.3.1.3 - 10.23.1.4.1.3.1.3 Method 3: Giving C-Nitrogen 9H-Pyrido[2,3-b]indoles [Seite 123]
8.1.4.1.3.1.4 - 10.23.1.4.1.3.1.4 Method 4: Giving C-Carbon 9H-Pyrido[2,3-b]indoles [Seite 124]
8.1.4.1.3.2 - 10.23.1.4.1.3.2 Substitution via Metalation [Seite 124]
8.1.4.1.3.3 - 10.23.1.4.1.3.3 Substitution via 1-Oxides [Seite 126]
8.1.4.1.3.4 - 10.23.1.4.1.3.4 Substitution via Displacement of Halogen [Seite 130]
8.1.4.1.3.4.1 - 10.23.1.4.1.3.4.1 Method 1: Direct Nucleophilic Displacement [Seite 130]
8.1.4.1.3.4.2 - 10.23.1.4.1.3.4.2 Method 2: Substitution of Halogen via Cross-Coupling Processes [Seite 133]
8.1.4.1.3.4.2.1 - 10.23.1.4.1.3.4.2.1 Variation 1: Forming Amines [Seite 133]
8.1.4.1.3.4.2.2 - 10.23.1.4.1.3.4.2.2 Variation 2: Forming Phenolic Ethers [Seite 135]
8.1.4.1.3.4.2.3 - 10.23.1.4.1.3.4.2.3 Variation 3: Adding Carbon Substituents [Seite 136]
8.1.4.2 - 10.23.1.4.2 Modification of Substituents [Seite 141]
8.1.4.2.1 - 10.23.1.4.2.1 Modification of C-Oxygen Functionalities [Seite 141]
8.1.4.2.1.1 - 10.23.1.4.2.1.1 Method 1: Giving C-Halogen [Seite 141]
8.1.4.2.1.2 - 10.23.1.4.2.1.2 Method 2: Giving Quinones [Seite 141]
8.1.4.2.1.3 - 10.23.1.4.2.1.3 Method 3: Giving Phenolic Ethers [Seite 142]
8.1.4.2.2 - 10.23.1.4.2.2 Modification of C-Nitrogen Functionalities [Seite 142]
8.1.4.2.2.1 - 10.23.1.4.2.2.1 Method 1: Giving C-Nitrogen 9H-Pyrido[2,3-b]indoles [Seite 142]
8.1.4.2.2.2 - 10.23.1.4.2.2.2 Method 2: Giving C-Halogen 9H-Pyrido[2,3-b]indoles [Seite 143]
8.1.4.2.2.3 - 10.23.1.4.2.2.3 Method 3: Giving C-Carbon 9H-Pyrido[2,3-b]indoles [Seite 143]
8.1.4.2.3 - 10.23.1.4.2.3 Modification of C-Carbon Functionalities [Seite 144]
8.1.4.2.3.1 - 10.23.1.4.2.3.1 Method 1: Giving C-Carbon 5H-Pyrido[3,2-b]indoles [Seite 144]
8.2 - 10.23.2 Product Subclass 2: 9H-Pyrido[3,4-b]indoles (?-Carbolines) [Seite 146]
8.2.1 - 10.23.2.1 Synthesis by Ring-Closure Reactions [Seite 146]
8.2.1.1 - 10.23.2.1.1 By Annulation to an Arene [Seite 146]
8.2.1.1.1 - 10.23.2.1.1.1 By Formation of One N-C and Two C-C Bonds [Seite 146]
8.2.1.1.1.1 - 10.23.2.1.1.1.1 With Formation of 1-2, 3-4, and 4a-9b Bonds [Seite 146]
8.2.1.1.1.1.1 - 10.23.2.1.1.1.1.1 Method 1: From 2,N-Dialkynyl-N-tosylanilines and Methyl Cyanoformate [Seite 146]
8.2.1.1.1.1.2 - 10.23.2.1.1.1.1.2 Method 2: By Intramolecular Reaction of a Cyano-Substituted 2,N-Dialkynyl-N-tosylaniline [Seite 147]
8.2.1.1.2 - 10.23.2.1.1.2 By Formation of One N-C Bond and One C-C Bond [Seite 148]
8.2.1.1.2.1 - 10.23.2.1.1.2.1 With Formation of 4a-4b and 9-9a Bonds [Seite 148]
8.2.1.1.2.1.1 - 10.23.2.1.1.2.1.1 Method 1: From (2-Aminophenyl)boronic Acid [Seite 148]
8.2.1.1.3 - 10.23.2.1.1.3 By Formation of Two C-C Bonds [Seite 149]
8.2.1.1.3.1 - 10.23.2.1.1.3.1 With Formation of 3-4 and 4a-9a Bonds [Seite 149]
8.2.1.1.3.1.1 - 10.23.2.1.1.3.1.1 Method 1: From 3-[(2-Alkynylphenyl)amino]pyrazin-2-ones [Seite 149]
8.2.1.1.4 - 10.23.2.1.1.4 By Formation of One N-C Bond [Seite 150]
8.2.1.1.4.1 - 10.23.2.1.1.4.1 With Formation of the 2-3 Bond [Seite 150]
8.2.1.1.4.1.1 - 10.23.2.1.1.4.1.1 Method 1: From 3-Alkynyl-1H-indole-2-carbaldehyde Oximes [Seite 150]
8.2.1.1.4.1.2 - 10.23.2.1.1.4.1.2 Method 2: From 3-Alkenyl-1H-indole-2-carbaldehyde Oximes [Seite 150]
8.2.1.1.4.1.3 - 10.23.2.1.1.4.1.3 Method 3: From 3-Alkynyl-1H-indole-2-carboxamides [Seite 151]
8.2.1.1.4.2 - 10.23.2.1.1.4.2 With Formation of the 8a-9 Bond [Seite 152]
8.2.1.1.4.2.1 - 10.23.2.1.1.4.2.1 Method 1: From 4-Aryl-3-nitropyridines [Seite 152]
8.2.1.1.4.2.2 - 10.23.2.1.1.4.2.2 Method 2: From 4-(2-Bromoaryl)pyridin-3-amines [Seite 153]
8.2.1.1.4.2.3 - 10.23.2.1.1.4.2.3 Method 3: From 3-Acetamido-4-(2-bromoaryl)-3,4-dihydropyridin-2-ones [Seite 154]
8.2.1.1.4.3 - 10.23.2.1.1.4.3 With Formation of the 9-9a Bond [Seite 154]
8.2.1.1.4.3.1 - 10.23.2.1.1.4.3.1 Method 1: From a 4-(2-Azidophenyl)pyridine by Thermolysis [Seite 154]
8.2.1.1.4.3.2 - 10.23.2.1.1.4.3.2 Method 2: From 4-(2-Azidoaryl)pyridinium Trifluoromethanesulfonates and a Rhodium Catalyst [Seite 155]
8.2.1.1.4.3.3 - 10.23.2.1.1.4.3.3 Method 3: From 4-(2-Nitroaryl)pyridines [Seite 157]
8.2.1.1.4.3.4 - 10.23.2.1.1.4.3.4 Method 4: From 2-(3-Halopyridin-4-yl)anilines [Seite 157]
8.2.1.1.4.3.5 - 10.23.2.1.1.4.3.5 Method 5: From N-[2-(3-Fluoropyridin-4-yl)phenyl]pivalamides [Seite 158]
8.2.1.1.4.3.6 - 10.23.2.1.1.4.3.6 Method 6: From 2-(2-Chloropyridin-4-yl)-N-tosylanilines [Seite 159]
8.2.1.1.5 - 10.23.2.1.1.5 By Formation of One C-C Bond [Seite 160]
8.2.1.1.5.1 - 10.23.2.1.1.5.1 With Formation of the 4a-4b Bond [Seite 160]
8.2.1.1.5.1.1 - 10.23.2.1.1.5.1.1 Method 1: From an N-Arylpyridin-3-amine by Irradiation [Seite 160]
8.2.1.1.5.1.2 - 10.23.2.1.1.5.1.2 Method 2: From N-(2-Haloaryl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation [Seite 161]
8.2.1.1.5.1.3 - 10.23.2.1.1.5.1.3 Method 3: From 4-Halo-N-phenylpyridin-3-amines by Intramolecular Palladium(0)-Catalyzed Bond Formation [Seite 163]
8.2.1.1.5.1.4 - 10.23.2.1.1.5.1.4 Method 4: From 4-Bromo-N-phenylpyridin-3-amines by Intramolecular Photostimulated SRN1 Reaction [Seite 163]
8.2.1.1.5.1.5 - 10.23.2.1.1.5.1.5 Method 5: From 4-Bromo-N-(2-bromophenyl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates [Seite 164]
8.2.1.1.5.1.6 - 10.23.2.1.1.5.1.6 Method 6: From an N-(2-Diazophenyl)-N-methylpyridin-3-amine [Seite 165]
8.2.1.2 - 10.23.2.1.2 By Annulation to a Heterocycle [Seite 165]
8.2.1.2.1 - 10.23.2.1.2.1 By Annulation to an Indole [Seite 165]
8.2.1.2.1.1 - 10.23.2.1.2.1.1 By Formation of Two N-C Bonds [Seite 166]
8.2.1.2.1.1.1 - 10.23.2.1.2.1.1.1 With Formation of 1-2 and 2-3 Bonds [Seite 166]
8.2.1.2.1.1.1.1 - 10.23.2.1.2.1.1.1.1 Method 1: From 1H-Indolic 1,5-Dicarbonyls and Ammonia [Seite 166]
8.2.1.2.1.1.1.1.1 - 10.23.2.1.2.1.1.1.1.1 Variation 1: From 2-Acyl-3-(2-ethoxyvinyl)-1H-indoles and Ammonia [Seite 167]
8.2.1.2.1.1.1.1.2 - 10.23.2.1.2.1.1.1.1.2 Variation 2: From Ethyl 3-[1-(Dimethylamino)-3-ethoxy-3-oxoprop-1-en-2-yl]-1-methyl-1H-indole-2-carboxylate [Seite 168]
8.2.1.2.1.1.1.1.3 - 10.23.2.1.2.1.1.1.1.3 Variation 3: From 3-Alkynyl-1H-indole-2-carbaldehydes and Ammonia [Seite 168]
8.2.1.2.1.1.1.1.4 - 10.23.2.1.2.1.1.1.1.4 Variation 4: From 2-Acyl-3-alkynyl-1H-indoles and Ammonia [Seite 169]
8.2.1.2.1.2 - 10.23.2.1.2.1.2 By Formation of One N-C Bond and One C-C Bond [Seite 170]
8.2.1.2.1.2.1 - 10.23.2.1.2.1.2.1 With Formation of 1-2 and 3-4 Bonds [Seite 170]
8.2.1.2.1.2.1.1 - 10.23.2.1.2.1.2.1.1 Method 1: From Ethyl 3-(2-Ethoxy-2-oxoethyl)-1H-indole-2-carboxylate. [Seite 170]
8.2.1.2.1.2.2 - 10.23.2.1.2.1.2.2 With Formation of 2-3 and 4-4a Bonds [Seite 171]
8.2.1.2.1.2.2.1 - 10.23.2.1.2.1.2.2.1 Method 1: From tert-Butylimines of 1H-Indole-2-carbaldehydes [Seite 171]
8.2.1.2.1.2.2.1.1 - 10.23.2.1.2.1.2.2.1.1 Variation 1: From tert-Butylimines of 3-Iodo-1H-indole-2-carbaldehydes [Seite 171]
8.2.1.2.1.2.2.1.2 - 10.23.2.1.2.1.2.2.1.2 Variation 2: From tert-Butylimines of 3-Unsubstituted 1H-Indole-2-carbaldehydes [Seite 172]
8.2.1.2.1.2.2.1.3 - 10.23.2.1.2.1.2.2.1.3 Variation 3: From O-Acetyloximes of 2-Acyl-1H-indoles and Internal Alkynes by a Copper/Rhodium Bimetallic Relay Catalyst [Seite 173]
8.2.1.2.1.2.2.1.4 - 10.23.2.1.2.1.2.2.1.4 Variation 4: From a 2-(1-Azidovinyl)-1H-indole with an Internal Alkyne and Copper/Rhodium Bimetallic Catalysis [Seite 174]
8.2.1.2.1.2.2.2 - 10.23.2.1.2.1.2.2.2 Method 2: From 1H-Indole-2-carboxamides [Seite 175]
8.2.1.2.1.2.2.2.1 - 10.23.2.1.2.1.2.2.2.1 Variation 1: From 1-Alkyl-1H-indole-2-carboxamides with Internal Alkynes and Palladium(II) Acetate [Seite 175]
8.2.1.2.1.2.2.2.2 - 10.23.2.1.2.1.2.2.2.2 Variation 2: From 1-Methyl-1H-indole-2-carboxamide with Diphenylacetylene and a Ruthenium Catalyst [Seite 176]
8.2.1.2.1.2.2.2.3 - 10.23.2.1.2.1.2.2.2.3 Variation 3: From 1-Alkyl-1H-indole-2-carboxamides with Ethynyl N-Methyliminodiacetic Acid (MIDA) Boronate and a Rhodium Catalyst [Seite 176]
8.2.1.2.1.2.2.2.4 - 10.23.2.1.2.1.2.2.2.4 Variation 4: From 1-Methyl-1H-indole-2-carboxamide with Vinyl Acetate [Seite 177]
8.2.1.2.1.2.2.3 - 10.23.2.1.2.1.2.2.3 Method 3: From 2-(Azidomethyl)-1H-indoles and Ynamides [Seite 177]
8.2.1.2.1.2.3 - 10.23.2.1.2.1.2.3 With Formation of 1-2 and 1-9a Bonds [Seite 179]
8.2.1.2.1.2.3.1 - 10.23.2.1.2.1.2.3.1 Method 1: From 2-(1H-Indol-3-yl)ethan-1-amines (Tryptamines) and Aldehydes [Seite 179]
8.2.1.2.1.2.3.1.1 - 10.23.2.1.2.1.2.3.1.1 Variation 1: With Hetaryl Aldehydes [Seite 179]
8.2.1.2.1.2.3.1.2 - 10.23.2.1.2.1.2.3.1.2 Variation 2: With a-Oxoaldehydes [Seite 184]
8.2.1.2.1.2.3.1.3 - 10.23.2.1.2.1.2.3.1.3 Variation 3: From Tryptamine with an Arylglyoxal and Palladium on Carbon [Seite 188]
8.2.1.2.1.2.3.1.4 - 10.23.2.1.2.1.2.3.1.4 Variation 4: With Aryl Methyl Ketones or Styrenes [Seite 189]
8.2.1.2.1.2.3.2 - 10.23.2.1.2.1.2.3.2 Method 2: From Tryptophan Esters or Amides and Trifluoroacetic Acid [Seite 190]
8.2.1.2.1.2.3.3 - 10.23.2.1.2.1.2.3.3 Method 3: From Iminophosphoranes [Seite 191]
8.2.1.2.1.2.4 - 10.23.2.1.2.1.2.4 With Formation of 2-3 and 1-9a Bonds [Seite 194]
8.2.1.2.1.2.4.1 - 10.23.2.1.2.1.2.4.1 Method 1: From 3-Alkenyl-1H-indoles and an Oxime [Seite 194]
8.2.1.2.1.3 - 10.23.2.1.2.1.3 By Formation of Two C-C Bonds [Seite 196]
8.2.1.2.1.3.1 - 10.23.2.1.2.1.3.1 With Formation of 1-9a and 4-4a Bonds [Seite 196]
8.2.1.2.1.3.1.1 - 10.23.2.1.2.1.3.1.1 Method 1: From a 1H-Indole and a 2-Aza-1,3-diene [Seite 196]
8.2.1.2.1.3.1.2 - 10.23.2.1.2.1.3.1.2 Method 2: From 1H-Indoles and 1,2,4-Triazines via Cycloaddition then Elimination of Nitrogen [Seite 198]
8.2.1.2.1.3.1.2.1 - 10.23.2.1.2.1.3.1.2.1 Variation 1: Intramolecularly from a 1-Acyl-1H-indole with a 1,2,4-Triazine Substituent [Seite 198]
8.2.1.2.1.3.1.2.2 - 10.23.2.1.2.1.3.1.2.2 Variation 2: Intramolecularly from a 1-Alkyl-1H-indole with a 1,2,4-Triazine Substituent [Seite 198]
8.2.1.2.1.3.1.2.3 - 10.23.2.1.2.1.3.1.2.3 Variation 3: Intermolecularly from 1H-Indoles and 1,2,4-Triazines [Seite 199]
8.2.1.2.1.3.1.2.4 - 10.23.2.1.2.1.3.1.2.4 Variation 4: From 1H-Indoles and 1,2,4-Triazines Generated In Situ [Seite 200]
8.2.1.2.1.4 - 10.23.2.1.2.1.4 By Formation of One N-C Bond [Seite 201]
8.2.1.2.1.4.1 - 10.23.2.1.2.1.4.1 With Formation of the 1-2 Bond [Seite 201]
8.2.1.2.1.4.1.1 - 10.23.2.1.2.1.4.1.1 Method 1: From a 2-[Bis(acetylsulfanyl)methyl]-1H-indole-3-pyruvate Oxime [Seite 201]
8.2.1.2.1.4.1.2 - 10.23.2.1.2.1.4.1.2 Method 2: From a 2-{2-[Bis(methylsulfanyl)methylene]-2,3-dihydroindol-3-yl}acetonitrile [Seite 202]
8.2.1.2.1.4.2 - 10.23.2.1.2.1.4.2 With Formation of the 2-3 Bond [Seite 202]
8.2.1.2.1.4.2.1 - 10.23.2.1.2.1.4.2.1 Method 1: From 2-Acyl-3-alkenyl-1H-indole Oximes [Seite 202]
8.2.1.2.1.4.2.2 - 10.23.2.1.2.1.4.2.2 Method 2: From 2-Acyl-3-alkynyl-1H-indole Imines or Oximes [Seite 204]
8.2.1.2.1.4.2.3 - 10.23.2.1.2.1.4.2.3 Method 3: From tert-Butylimines of 3-Alkynyl-1H-indole-2-carbaldehydes [Seite 206]
8.2.1.2.1.4.2.4 - 10.23.2.1.2.1.4.2.4 Method 4: From 3-Alkynyl-2-(azidomethyl)-1H-indoles [Seite 207]
8.2.1.2.1.5 - 10.23.2.1.2.1.5 By Formation of One C-C Bond [Seite 207]
8.2.1.2.1.5.1 - 10.23.2.1.2.1.5.1 With Formation of the 1-9a Bond [Seite 207]
8.2.1.2.1.5.1.1 - 10.23.2.1.2.1.5.1.1 Method 1: From N-Acyltryptamines [Seite 207]
8.2.1.2.1.5.2 - 10.23.2.1.2.1.5.2 With Formation of the 4-4a Bond [Seite 210]
8.2.1.2.1.5.2.1 - 10.23.2.1.2.1.5.2.1 Method 1: From N-(2,2-Dialkoxyethyl)-1H-indole-2-carboxamides [Seite 210]
8.2.1.2.1.5.2.2 - 10.23.2.1.2.1.5.2.2 Method 2: From an N-Allyl-3-iodo-1H-indole-2-carboxamide [Seite 212]
8.2.1.2.1.5.2.3 - 10.23.2.1.2.1.5.2.3 Method 3: From an N-(2-Oxoalkyl)-1H-indole-2-carboxamide [Seite 212]
8.2.1.2.1.5.2.4 - 10.23.2.1.2.1.5.2.4 Method 4: From an N-Propargyl-1H-indole-2-carboxamide [Seite 215]
8.2.2 - 10.23.2.2 Synthesis by Ring Transformation [Seite 215]
8.2.2.1 - 10.23.2.2.1 Method 1: From 1-(3-Pyridyl)-1H-benzotriazoles [Seite 215]
8.2.2.2 - 10.23.2.2.2 Method 2: From 3-Aryl-3H-1,2,3-triazolo[4,5-c]pyridines [Seite 216]
8.2.2.3 - 10.23.2.2.3 Method 3: From 4-[(1H-Indol-3-yl)methyl]oxazol-5(4H)-ones [Seite 216]
8.2.2.4 - 10.23.2.2.4 Method 4: From Pyrano[3,4-b]indol-3(9H)-ones [Seite 217]
8.2.3 - 10.23.2.3 Aromatization [Seite 218]
8.2.3.1 - 10.23.2.3.1 Method 1: From 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indoles [Seite 219]
8.2.3.2 - 10.23.2.3.2 Method 2: From 4,9-Dihydro-3H-pyrido[3,4-b]indoles [Seite 228]
8.2.3.3 - 10.23.2.3.3 Method 3: From 2-Aryl-4,9-dihydro-3H-pyrido[3,4-b]indol-2-iums [Seite 233]
8.2.3.4 - 10.23.2.3.4 Method 4: From 2,9-Dihydro-1H-pyrido[3,4-b]indoles [Seite 233]
8.2.3.5 - 10.23.2.3.5 Method 5: From 6,7,8,9-Tetrahydro-5H-pyrido[3,4-b]indoles [Seite 237]
8.2.4 - 10.23.2.4 Synthesis by Substituent Modification [Seite 238]
8.2.4.1 - 10.23.2.4.1 Substitution of Existing Substituents [Seite 238]
8.2.4.1.1 - 10.23.2.4.1.1 Substitution of N-Hydrogen [Seite 238]
8.2.4.1.1.1 - 10.23.2.4.1.1.1 Giving N-Carbon 9H-Pyrido[3,4-b]indoles [Seite 238]
8.2.4.1.1.1.1 - 10.23.2.4.1.1.1.1 Method 1: 9-Alkylation Using an Alkyl Halide [Seite 238]
8.2.4.1.1.1.2 - 10.23.2.4.1.1.1.2 Method 2: 9-Arylation Using an Aryl Halide [Seite 240]
8.2.4.1.1.1.3 - 10.23.2.4.1.1.1.3 Method 3: 9-Acylation [Seite 242]
8.2.4.1.1.1.4 - 10.23.2.4.1.1.1.4 Method 4: 2-Alkylation Giving 2-Alkyl-9H-pyrido[3,4-b]indol-2-ium Salts and thence 2-Alkyl-2H-pyrido[3,4-b]indoles [Seite 243]
8.2.4.1.2 - 10.23.2.4.1.2 Substitution of N-Carbon and N-Sulfur [Seite 247]
8.2.4.1.2.1 - 10.23.2.4.1.2.1 Giving N-Hydrogen 9H-Pyrido[3,4-b]indoles [Seite 247]
8.2.4.1.2.1.1 - 10.23.2.4.1.2.1.1 Method 1: N-Deprotection [Seite 247]
8.2.4.1.3 - 10.23.2.4.1.3 Substitution of C-Hydrogen [Seite 248]
8.2.4.1.3.1 - 10.23.2.4.1.3.1 Direct Substitution by Electrophiles [Seite 248]
8.2.4.1.3.1.1 - 10.23.2.4.1.3.1.1 Method 1: Giving C-Halogen 9H-Pyrido[3,4-b]indoles [Seite 248]
8.2.4.1.3.1.2 - 10.23.2.4.1.3.1.2 Method 2: Giving C-Sulfur 9H-Pyrido[3,4-b]indoles [Seite 250]
8.2.4.1.3.1.3 - 10.23.2.4.1.3.1.3 Method 3: Giving C-Nitrogen 9H-Pyrido[3,4-b]indoles [Seite 251]
8.2.4.1.3.1.4 - 10.23.2.4.1.3.1.4 Method 4: Giving C-Carbon 9H-Pyrido[3,4-b]indoles [Seite 252]
8.2.4.1.3.2 - 10.23.2.4.1.3.2 Direct Substitution by Radicals [Seite 253]
8.2.4.1.3.3 - 10.23.2.4.1.3.3 Substitution via Metalation [Seite 255]
8.2.4.1.3.4 - 10.23.2.4.1.3.4 Substitution via 2-Oxides (N-Oxides) [Seite 256]
8.2.4.1.3.4.1 - 10.23.2.4.1.3.4.1 Variation 1: With Formation of 9H-Pyrido[3,4-b]indole-1-carbonitriles [Seite 257]
8.2.4.1.3.4.2 - 10.23.2.4.1.3.4.2 Variation 2: With Formation of 9H-Pyrido[3,4-b]indol-1-ols (2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones) [Seite 258]
8.2.4.1.3.4.3 - 10.23.2.4.1.3.4.3 Variation 3: With Formation of 1-Halo-9H-pyrido[3,4-b]indoles [Seite 260]
8.2.4.1.3.4.4 - 10.23.2.4.1.3.4.4 Variation 4: With Formation of 1-Carbon-9H-pyrido[3,4-b]indoles [Seite 260]
8.2.4.1.3.5 - 10.23.2.4.1.3.5 Substitution via Displacement of Halogen [Seite 261]
8.2.4.1.3.5.1 - 10.23.2.4.1.3.5.1 Method 1: Direct Nucleophilic Displacement [Seite 261]
8.2.4.1.3.5.1.1 - 10.23.2.4.1.3.5.1.1 Variation 1: With Formation of Amines [Seite 261]
8.2.4.1.3.5.1.2 - 10.23.2.4.1.3.5.1.2 Variation 2: With Formation of Ethers [Seite 262]
8.2.4.1.3.5.1.3 - 10.23.2.4.1.3.5.1.3 Variation 3: With Formation of Halides [Seite 262]
8.2.4.1.3.5.2 - 10.23.2.4.1.3.5.2 Method 2: Substitution of Halogen (or Trifluoromethanesulfonate) via Cross-Coupling Processes [Seite 263]
8.2.4.1.3.5.2.1 - 10.23.2.4.1.3.5.2.1 Variation 1: Reaction at C1 [Seite 263]
8.2.4.1.3.5.2.2 - 10.23.2.4.1.3.5.2.2 Variation 2: Reaction at C4 [Seite 266]
8.2.4.1.3.5.2.3 - 10.23.2.4.1.3.5.2.3 Variation 3: Reaction at Benzene Ring Positions [Seite 267]
8.2.4.1.3.6 - 10.23.2.4.1.3.6 Substitution via Displacement of Oxygen [Seite 268]
8.2.4.2 - 10.23.2.4.2 Modification of Substituents [Seite 268]
8.2.4.2.1 - 10.23.2.4.2.1 Modification of C-Oxygen Functionalities [Seite 268]
8.2.4.2.1.1 - 10.23.2.4.2.1.1 Method 1: Giving C-Halogen [Seite 268]
8.2.4.2.1.2 - 10.23.2.4.2.1.2 Method 2: Giving C-Oxygen [Seite 269]
8.2.4.2.2 - 10.23.2.4.2.2 Modification of C-Nitrogen Functionalities [Seite 272]
8.2.4.2.2.1 - 10.23.2.4.2.2.1 Method 1: Giving C-Nitrogen [Seite 272]
8.2.4.2.2.2 - 10.23.2.4.2.2.2 Method 2: Giving C-Halogen [Seite 274]
8.2.4.2.2.3 - 10.23.2.4.2.2.3 Method 3: Giving C-Oxygen [Seite 274]
8.2.4.2.3 - 10.23.2.4.2.3 Modification of C-Carbon Functionalities [Seite 276]
8.2.4.2.3.1 - 10.23.2.4.2.3.1 Method 1: Giving C-Carbon 9H-Pyrido[3,4-b]indoles [Seite 276]
8.2.4.2.3.1.1 - 10.23.2.4.2.3.1.1 Variation 1: From Alkyl-Substituted 9H-Pyrido[3,4-b]indoles [Seite 276]
8.2.4.2.3.1.2 - 10.23.2.4.2.3.1.2 Variation 2: From 9H-Pyrido[3,4-b]indolyl Alcohols [Seite 277]
8.2.4.2.3.1.3 - 10.23.2.4.2.3.1.3 Variation 3: From 9H-Pyrido[3,4-b]indolyl Aldehydes and Ketones [Seite 278]
8.2.4.2.3.1.4 - 10.23.2.4.2.3.1.4 Variation 4: From 9H-Pyrido[3,4-b]indole Acids, Esters, and Amides [Seite 279]
8.2.4.2.3.2 - 10.23.2.4.2.3.2 Method 2: Giving C-Nitrogen 9H-Pyrido[3,4-b]indoles [Seite 281]
8.2.4.2.3.3 - 10.23.2.4.2.3.3 Method 3: Giving C-Hydrogen 9H-Pyrido[3,4-b]indoles [Seite 283]
8.3 - 10.23.3 Product Subclass 3: 5H-Pyrido[4,3-b]indoles (?-Carbolines) [Seite 283]
8.3.1 - 10.23.3.1 Synthesis by Ring-Closure Reactions [Seite 283]
8.3.1.1 - 10.23.3.1.1 By Annulation to an Arene [Seite 283]
8.3.1.1.1 - 10.23.3.1.1.1 By Formation of One N-C and Two C-C Bonds [Seite 283]
8.3.1.1.1.1 - 10.23.3.1.1.1.1 With Formation of 1-2, 3-4, and 4a-9b Bonds [Seite 283]
8.3.1.1.1.1.1 - 10.23.3.1.1.1.1.1 Method 1: From 2,N-Dialkynyl-N-tosylanilines and Methyl Cyanoformate [Seite 283]
8.3.1.1.2 - 10.23.3.1.1.2 By Formation of One N-C Bond and One C-C Bond [Seite 284]
8.3.1.1.2.1 - 10.23.3.1.1.2.1 With Formation of 4a-5 and 9a-9b Bonds [Seite 284]
8.3.1.1.2.1.1 - 10.23.3.1.1.2.1.1 Method 1: From Arylhydrazines [Seite 284]
8.3.1.1.2.1.1.1 - 10.23.3.1.1.2.1.1.1 Variation 1: Using a 4-Hydroxypyridin-2-one [Seite 284]
8.3.1.1.2.1.1.2 - 10.23.3.1.1.2.1.1.2 Variation 2: Using 1-Acetyl-3-bromopiperidin-4-one [Seite 285]
8.3.1.1.2.1.2 - 10.23.3.1.1.2.1.2 Method 2: From 4-Fluoro-3-iodopyridine [Seite 286]
8.3.1.1.2.2 - 10.23.3.1.1.2.2 With Formation of 1-2 and 1-9b Bonds [Seite 287]
8.3.1.1.2.2.1 - 10.23.3.1.1.2.2.1 Method 1: From Iminophosphoranes [Seite 287]
8.3.1.1.3 - 10.23.3.1.1.3 By Formation of One N-C Bond [Seite 289]
8.3.1.1.3.1 - 10.23.3.1.1.3.1 With Formation of the 4a-5 Bond [Seite 289]
8.3.1.1.3.1.1 - 10.23.3.1.1.3.1.1 Method 1: From 3-(2-Azidoaryl)pyridines [Seite 289]
8.3.1.1.3.1.1.1 - 10.23.3.1.1.3.1.1.1 Variation 1: From 3-(2-Azidoaryl)pyridinium Salts and a Ruthenium Catalyst [Seite 289]
8.3.1.1.3.1.2 - 10.23.3.1.1.3.1.2 Method 2: From 3-(2-Nitrosoaryl)pyridines [Seite 291]
8.3.1.1.3.1.3 - 10.23.3.1.1.3.1.3 Method 3: From 2-(3-Pyridyl)-N-tosylanilines or N-Acetyl-2-(3-pyridyl)-anilines [Seite 291]
8.3.1.1.3.1.4 - 10.23.3.1.1.3.1.4 Method 4: From 4-Fluoro-3-(2-pivaloylaminophenyl)pyridine [Seite 292]
8.3.1.1.4 - 10.23.3.1.1.4 By Formation of One C-C Bond [Seite 293]
8.3.1.1.4.1 - 10.23.3.1.1.4.1 With Formation of the 9a-9b Bond [Seite 293]
8.3.1.1.4.1.1 - 10.23.3.1.1.4.1.1 Method 1: From N-Arylpyridin-4-amines [Seite 293]
8.3.1.1.4.1.2 - 10.23.3.1.1.4.1.2 Method 2: From an N-Arylpyridin-4-amine with at Least One Halogen on at Least One Ring [Seite 294]
8.3.1.1.4.1.2.1 - 10.23.3.1.1.4.1.2.1 Variation 1: From an N-(2-Bromophenyl)pyridin-4-amine [Seite 294]
8.3.1.1.4.1.2.2 - 10.23.3.1.1.4.1.2.2 Variation 2: From an N-Aryl-3-bromopyridin-4-amine [Seite 294]
8.3.1.1.4.1.2.3 - 10.23.3.1.1.4.1.2.3 Variation 3: From an N-(2-Bromophenyl)-3-bromopyridin-4-amine by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates [Seite 295]
8.3.1.1.4.1.3 - 10.23.3.1.1.4.1.3 Method 3: From N-Aryl-3-halopyridin-4-amines by Photostimulated SRN1 Reactions [Seite 296]
8.3.1.2 - 10.23.3.1.2 By Annulation to a Heterocycle [Seite 296]
8.3.1.2.1 - 10.23.3.1.2.1 By Annulation to a Pyridine [Seite 296]
8.3.1.2.2 - 10.23.3.1.2.2 By Annulation to an Indole [Seite 297]
8.3.1.2.2.1 - 10.23.3.1.2.2.1 By Formation of Two N-C and One C-C Bonds [Seite 297]
8.3.1.2.2.1.1 - 10.23.3.1.2.2.1.1 With Formation of 1-2, 2-3, and 4-4a Bonds [Seite 297]
8.3.1.2.2.1.1.1 - 10.23.3.1.2.2.1.1.1 Method 1: From 3-Acetyl-1H-indole, an Alkyne and a Primary Amine [Seite 297]
8.3.1.2.2.1.2 - 10.23.3.1.2.2.1.2 With Formation of 1-2, 2-3, and 3-4 Bonds [Seite 298]
8.3.1.2.2.1.2.1 - 10.23.3.1.2.2.1.2.1 Method 1: From 2-(2-Oxoalkyl)-1H-indole-3-carbaldehydes and Aryl Aldehydes [Seite 298]
8.3.1.2.2.2 - 10.23.3.1.2.2.2 By Formation of Two N-C Bonds [Seite 299]
8.3.1.2.2.2.1 - 10.23.3.1.2.2.2.1 With Formation of 1-2 and 2-3 Bonds [Seite 299]
8.3.1.2.2.2.1.1 - 10.23.3.1.2.2.2.1.1 Method 1: From 2-(3-Acetyl-1H-indol-2-yl)acetonitrile [Seite 299]
8.3.1.2.2.2.1.2 - 10.23.3.1.2.2.2.1.2 Method 2: From 2-(3-Formyl-1H-indol-2-yl)acrylates [Seite 300]
8.3.1.2.2.2.1.2.1 - 10.23.3.1.2.2.2.1.2.1 Variation 1: From a 2-Alkynyl-1H-indole-3-carbaldehyde [Seite 301]
8.3.1.2.2.2.1.2.2 - 10.23.3.1.2.2.2.1.2.2 Variation 2: From a 2-Alkenyl-1H-indole-3-carbaldehyde [Seite 301]
8.3.1.2.2.2.1.3 - 10.23.3.1.2.2.2.1.3 Method 3: From (3-Acyl-1H-indol-2-yl)malonates [Seite 302]
8.3.1.2.2.3 - 10.23.3.1.2.2.3 By Formation of One N-C Bond and One C-C Bond [Seite 304]
8.3.1.2.2.3.1 - 10.23.3.1.2.2.3.1 With Formation of 2-3 and 3-4 Bonds [Seite 304]
8.3.1.2.2.3.1.1 - 10.23.3.1.2.2.3.1.1 Method 1: From Secondary 2-Alkyl-1H-indole-3-carboxamides [Seite 304]
8.3.1.2.2.3.2 - 10.23.3.1.2.2.3.2 With Formation of 2-3 and 4-4a Bonds [Seite 306]
8.3.1.2.2.3.2.1 - 10.23.3.1.2.2.3.2.1 Method 1: From Oxime O-Methyl Ethers of 1H-Indol-3-yl Aldehydes or Ketones [Seite 306]
8.3.1.2.2.3.2.1.1 - 10.23.3.1.2.2.3.2.1.1 Variation 1: Reaction with Alkynes and Alkenes [Seite 306]
8.3.1.2.2.3.2.1.2 - 10.23.3.1.2.2.3.2.1.2 Variation 2: Reaction with Diphenylacetylene under Rhodium Catalysis [Seite 308]
8.3.1.2.2.3.2.2 - 10.23.3.1.2.2.3.2.2 Method 2: From Tosylhydrazones of 1H-Indol-3-yl Aldehydes and Ketones [Seite 308]
8.3.1.2.2.3.2.3 - 10.23.3.1.2.2.3.2.3 Method 3: From tert-Butylimines of 1H-Indole-3-carbaldehydes [Seite 310]
8.3.1.2.2.3.2.3.1 - 10.23.3.1.2.2.3.2.3.1 Variation 1: From tert-Butylimines of 2-Halo-1H-indole-3-carbaldehydes [Seite 310]
8.3.1.2.2.3.2.3.2 - 10.23.3.1.2.2.3.2.3.2 Variation 2: From tert-Butylimines of 2-Unsubstituted 1H-Indole-3-carbaldehydes [Seite 312]
8.3.1.2.2.3.2.4 - 10.23.3.1.2.2.3.2.4 Method 4: From N-Methoxy or N-Alkyl/Aryl 1-Methyl-1H-indole-3-carboxamides [Seite 313]
8.3.1.2.2.4 - 10.23.3.1.2.2.4 By Formation of Two C-C Bonds [Seite 314]
8.3.1.2.2.4.1 - 10.23.3.1.2.2.4.1 With Formation of 1-9b and 4-4a Bonds [Seite 314]
8.3.1.2.2.4.1.1 - 10.23.3.1.2.2.4.1.1 Method 1: From Triethyl 1,2,4-Triazine-3,5,6-tricarboxylate [Seite 314]
8.3.1.2.2.5 - 10.23.3.1.2.2.5 By Formation of One N-C Bond [Seite 315]
8.3.1.2.2.5.1 - 10.23.3.1.2.2.5.1 With Formation of the 1-2 Bond [Seite 315]
8.3.1.2.2.5.1.1 - 10.23.3.1.2.2.5.1.1 Method 1: From a 3-Methyl-1H-indole-2-carbaldehyde [Seite 315]
8.3.1.2.2.5.2 - 10.23.3.1.2.2.5.2 With Formation of the 2-3 Bond [Seite 316]
8.3.1.2.2.5.2.1 - 10.23.3.1.2.2.5.2.1 Method 1: From a 3-Acyl-2-alkenyl-1H-indole Oxime [Seite 316]
8.3.1.2.2.5.2.2 - 10.23.3.1.2.2.5.2.2 Method 2: From tert-Butylimines of 2-Alkynyl-1H-indole-3-carbaldehydes [Seite 317]
8.3.1.2.2.6 - 10.23.3.1.2.2.6 By Formation of One C-C Bond [Seite 319]
8.3.1.2.2.6.1 - 10.23.3.1.2.2.6.1 With Formation of the 4-4a Bond [Seite 319]
8.3.1.2.2.6.1.1 - 10.23.3.1.2.2.6.1.1 Method 1: From 3-{[(2,2-Diethoxyethyl)imino]methyl}-1H-indoles [Seite 319]
8.3.1.2.2.6.1.1.1 - 10.23.3.1.2.2.6.1.1.1 Variation 1: From 3-{[(2,2-Diethoxyethyl)amino]methyl}-1H-indoles [Seite 320]
8.3.1.2.2.6.1.2 - 10.23.3.1.2.2.6.1.2 Method 2: From Ethyl [(1H-Indol-3-yl)methyl]glycinates [Seite 321]
8.3.1.2.2.6.1.3 - 10.23.3.1.2.2.6.1.3 Method 3: From N-Allyl-2-iodo-1H-indole-3-carboxamides [Seite 322]
8.3.2 - 10.23.3.2 Synthesis by Ring Transformation [Seite 323]
8.3.2.1 - 10.23.3.2.1 Method 1: From 1-(4-Pyridyl)-1H-benzotriazoles [Seite 323]
8.3.2.2 - 10.23.3.2.2 Method 2: From 1-Aryl-1H-1,2,3-triazolo[4,5-c]pyridines [Seite 325]
8.3.2.3 - 10.23.3.2.3 Method 3: By Ring Expansion of 5-Azidocyclopent-2-en-1-ols To Form Pyridines [Seite 325]
8.3.3 - 10.23.3.3 Aromatization [Seite 326]
8.3.3.1 - 10.23.3.3.1 Method 1: From Tetrahydro-5H-pyrido[4,3-b]indoles and Octahydro-5H-pyrido[4,3-b]indoles [Seite 326]
8.3.3.2 - 10.23.3.3.2 Method 2: From Dihydro-5H-pyrido[4,3-b]indoles [Seite 330]
8.3.4 - 10.23.3.4 Synthesis by Substituent Modification [Seite 333]
8.3.4.1 - 10.23.3.4.1 Substitution of Existing Substituents [Seite 333]
8.3.4.1.1 - 10.23.3.4.1.1 Substitution of N-Hydrogen [Seite 333]
8.3.4.1.1.1 - 10.23.3.4.1.1.1 Giving N-Sulfur 5H-Pyrido[4,3-b]indoles [Seite 333]
8.3.4.1.1.2 - 10.23.3.4.1.1.2 Giving N-Carbon 5H-Pyrido[4,3-b]indoles [Seite 334]
8.3.4.1.1.2.1 - 10.23.3.4.1.1.2.1 Method 1: 5-Alkylation Using an Alkyl Halide [Seite 334]
8.3.4.1.1.2.2 - 10.23.3.4.1.1.2.2 Method 2: 5-Arylation Using an Aryl Halide [Seite 336]
8.3.4.1.1.2.3 - 10.23.3.4.1.1.2.3 Method 3: 2-Alkylation Giving 2-Alkyl-5H-pyrido[4,3-b]indol-2-ium Salts and thence 5-Alkylation [Seite 336]
8.3.4.1.2 - 10.23.3.4.1.2 Substitution of N-Carbon and N-Sulfur [Seite 338]
8.3.4.1.2.1 - 10.23.3.4.1.2.1 Giving N-Hydrogen 5H-Pyrido[4,3-b]indoles [Seite 338]
8.3.4.1.2.1.1 - 10.23.3.4.1.2.1.1 Method 1: N-Deprotection [Seite 338]
8.3.4.1.3 - 10.23.3.4.1.3 Substitution of C-Hydrogen [Seite 339]
8.3.4.1.3.1 - 10.23.3.4.1.3.1 Direct Substitution by Electrophiles [Seite 339]
8.3.4.1.3.1.1 - 10.23.3.4.1.3.1.1 Method 1: Giving C-Halogen [Seite 339]
8.3.4.1.3.1.2 - 10.23.3.4.1.3.1.2 Method 2: Giving C-Sulfur [Seite 339]
8.3.4.1.3.1.3 - 10.23.3.4.1.3.1.3 Method 3: Giving C-Nitrogen [Seite 340]
8.3.4.1.3.1.4 - 10.23.3.4.1.3.1.4 Method 4: Giving C-Carbon [Seite 340]
8.3.4.1.3.2 - 10.23.3.4.1.3.2 Substitution via Metalation [Seite 341]
8.3.4.1.3.3 - 10.23.3.4.1.3.3 Substitution via 2-Oxides [Seite 342]
8.3.4.1.3.4 - 10.23.3.4.1.3.4 Substitution via Displacement of Halogen [Seite 344]
8.3.4.1.3.4.1 - 10.23.3.4.1.3.4.1 Method 1: Direct Nucleophilic Displacement [Seite 344]
8.3.4.1.3.4.2 - 10.23.3.4.1.3.4.2 Method 2: Substitution of Halogen via Cross-Coupling Processes [Seite 347]
8.3.4.2 - 10.23.3.4.2 Modification of Substituents [Seite 350]
8.3.4.2.1 - 10.23.3.4.2.1 Modification of C-Oxygen Functionalities [Seite 350]
8.3.4.2.1.1 - 10.23.3.4.2.1.1 Method 1: Giving C-Halogen [Seite 350]
8.3.4.2.2 - 10.23.3.4.2.2 Modification of C-Nitrogen Functionalities [Seite 351]
8.3.4.2.2.1 - 10.23.3.4.2.2.1 Method 1: Giving C-Nitrogen [Seite 351]
8.3.4.2.3 - 10.23.3.4.2.3 Modification of C-Carbon Functionalities [Seite 351]
8.3.4.2.3.1 - 10.23.3.4.2.3.1 Method 1: Giving C-Carbon 5H-Pyrido[4,3-b]indoles [Seite 351]
8.3.4.2.3.2 - 10.23.3.4.2.3.2 Method 2: Giving C-Nitrogen 5H-Pyrido[4,3-b]indoles [Seite 352]
8.3.4.2.3.3 - 10.23.3.4.2.3.3 Method 3: Giving C-Hydrogen 5H-Pyrido[4,3-b]indoles [Seite 352]
8.4 - 10.23.4 Product Subclass 4: 5H-Pyrido[3,2-b]indoles (?-Carbolines) [Seite 353]
8.4.1 - 10.23.4.1 Synthesis by Ring-Closure Reactions [Seite 353]
8.4.1.1 - 10.23.4.1.1 By Annulation to an Arene [Seite 353]
8.4.1.1.1 - 10.23.4.1.1.1 By Formation of One N-C and Two C-C Bonds [Seite 353]
8.4.1.1.1.1 - 10.23.4.1.1.1.1 With Formation of 2-3, 4a-5, and 9a-9b Bonds [Seite 353]
8.4.1.1.1.1.1 - 10.23.4.1.1.1.1.1 Method 1: From 2-Iodoanilines and N-Tosyl Enynamines [Seite 353]
8.4.1.1.2 - 10.23.4.1.1.2 By Formation of Two N-C Bonds [Seite 354]
8.4.1.1.2.1 - 10.23.4.1.1.2.1 With Formation of 4a-5 and 5-5a Bonds [Seite 354]
8.4.1.1.2.1.1 - 10.23.4.1.1.2.1.1 Method 1: From Primary Amines and 3-Bromo-2-(2-bromophenyl)pyridine [Seite 354]
8.4.1.1.3 - 10.23.4.1.1.3 By Formation of Two C-C Bonds [Seite 355]
8.4.1.1.3.1 - 10.23.4.1.1.3.1 With Formation of 2-3 and 4a-9b Bonds [Seite 355]
8.4.1.1.3.1.1 - 10.23.4.1.1.3.1.1 Method 1: From 2-(Aminomethyl)aniline Cinnamaldehyde Diimine [Seite 355]
8.4.1.1.4 - 10.23.4.1.1.4 By Formation of One N-C Bond [Seite 356]
8.4.1.1.4.1 - 10.23.4.1.1.4.1 With Formation of the 4a-5 Bond [Seite 356]
8.4.1.1.4.1.1 - 10.23.4.1.1.4.1.1 Method 1: From 1-Methyl-2-(2-Azidoaryl)pyridinium Trifluoromethanesulfonates [Seite 356]
8.4.1.1.4.1.2 - 10.23.4.1.1.4.1.2 Method 2: From 3-Fluoro-2-[2-(pivaloylamino)phenyl]pyridines [Seite 357]
8.4.1.1.4.2 - 10.23.4.1.1.4.2 With Formation of the 5-5a Bond [Seite 359]
8.4.1.1.4.2.1 - 10.23.4.1.1.4.2.1 Method 1: From 3-Azido-2-phenylpyridine [Seite 359]
8.4.1.1.4.2.2 - 10.23.4.1.1.4.2.2 Method 2: From 2-Aryl-3-nitropyridines [Seite 360]
8.4.1.1.4.2.3 - 10.23.4.1.1.4.2.3 Method 3: From 2-(2-Chlorophenyl)pyridin-3-amine by Intramolecular Photostimulated SRN1 Reaction [Seite 361]
8.4.1.1.5 - 10.23.4.1.1.5 By Formation of One C-C Bond [Seite 362]
8.4.1.1.5.1 - 10.23.4.1.1.5.1 With Formation of the 9a-9b Bond [Seite 362]
8.4.1.1.5.1.1 - 10.23.4.1.1.5.1.1 Method 1: From N-Arylpyridin-3-amines by Irradiation [Seite 362]
8.4.1.1.5.1.2 - 10.23.4.1.1.5.1.2 Method 2: From N-Arylpyridin-3-amines by Palladium(0)-Catalyzed Bond Formation [Seite 363]
8.4.1.1.5.1.2.1 - 10.23.4.1.1.5.1.2.1 Variation 1: From Cyclohexanone and Pyridin-3-amine [Seite 364]
8.4.1.1.5.1.3 - 10.23.4.1.1.5.1.3 Method 3: From N-(2-Halophenyl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation [Seite 364]
8.4.1.1.5.1.4 - 10.23.4.1.1.5.1.4 Method 4: From N-Aryl-2-halopyridin-3-amines by Intramolecular Palladium(0)-Catalyzed Bond Formation [Seite 365]
8.4.1.1.5.1.5 - 10.23.4.1.1.5.1.5 Method 5: From N-Aryl-2-bromopyridin-3-amines by Intramolecular Photostimulated SRN1 Reaction [Seite 367]
8.4.1.1.5.1.6 - 10.23.4.1.1.5.1.6 Method 6: From 2-Bromo-N-(2-bromophenyl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates [Seite 367]
8.4.1.1.5.1.7 - 10.23.4.1.1.5.1.7 Method 7: From an N-(2-Diazophenyl)-N-methylpyridin-3-amine [Seite 368]
8.4.1.2 - 10.23.4.1.2 By Annulation to a Heterocycle [Seite 368]
8.4.1.2.1 - 10.23.4.1.2.1 By Annulation to a Pyridine [Seite 368]
8.4.1.2.1.1 - 10.23.4.1.2.1.1 By Formation of One N-C Bond and One C-C Bond [Seite 368]
8.4.1.2.1.1.1 - 10.23.4.1.2.1.1.1 With Formation of 5-5a and 9a-9b Bonds [Seite 368]
8.4.1.2.1.1.1.1 - 10.23.4.1.2.1.1.1.1 Method 1: From Benzyne and an N-Tosylpyridinium Imide [Seite 368]
8.4.1.2.2 - 10.23.4.1.2.2 By Annulation to an Indole [Seite 370]
8.4.1.2.2.1 - 10.23.4.1.2.2.1 By Formation of One N-C and Two C-C Bonds [Seite 370]
8.4.1.2.2.1.1 - 10.23.4.1.2.2.1.1 With Formation of 1-9b, 2-3, and 4-4a Bonds [Seite 370]
8.4.1.2.2.1.1.1 - 10.23.4.1.2.2.1.1.1 Method 1: From 3-Acetyl-1H-indole Oxime and Acetylene [Seite 370]
8.4.1.2.2.1.2 - 10.23.4.1.2.2.1.2 With Formation of 1-2, 2-3, and 4-4a Bonds [Seite 371]
8.4.1.2.2.1.2.1 - 10.23.4.1.2.2.1.2.1 Method 1: From N-(tert-Butoxycarbonyl)indol-3-amines, Aryl Aldehydes, and Terminal Arylalkynes [Seite 371]
8.4.1.2.2.2 - 10.23.4.1.2.2.2 By Formation of One N-C Bond and One C-C Bond [Seite 373]
8.4.1.2.2.2.1 - 10.23.4.1.2.2.2.1 With Formation of 1-9b and 3-4 Bonds [Seite 373]
8.4.1.2.2.2.1.1 - 10.23.4.1.2.2.2.1.1 Method 1: From 2-[Bis(methylsulfanyl)methylene]-1-methyl-1,3-dihydro-2H-indol-3-one and a ß-(Lithioamino)acrylonitrile [Seite 373]
8.4.1.2.2.2.1.1.1 - 10.23.4.1.2.2.2.1.1.1 Variation 1: From 2-[Bis(methylsulfanyl)methylene]-1-methyl-1,3-dihydro-2H-indol-3-one and Malononitrile [Seite 374]
8.4.1.2.2.2.2 - 10.23.4.1.2.2.2.2 With Formation of 1-2 and 4-4a Bonds [Seite 374]
8.4.1.2.2.2.2.1 - 10.23.4.1.2.2.2.2.1 Method 1: From an N-Acetyl-1H-indol-3-amine and a 1,3-Dialdehyde Equivalent [Seite 374]
8.4.1.2.3 - 10.23.4.1.2.3 By Annulation to a 1H-Pyrrolo[3,2-b]pyridine (a 4-Azaindole) [Seite 375]
8.4.1.2.3.1 - 10.23.4.1.2.3.1 By Formation of Two C-C Bonds [Seite 375]
8.4.1.2.3.1.1 - 10.23.4.1.2.3.1.1 With Formation of 7-8 and 9-9a Bonds [Seite 375]
8.4.1.2.3.1.1.1 - 10.23.4.1.2.3.1.1.1 Method 1: From a 2-Vinyl-1H-Pyrrolo[3,2-b]pyridine and Dimethyl Acetylenedicarboxylate [Seite 375]
8.4.2 - 10.23.4.2 Synthesis by Ring Transformation [Seite 376]
8.4.2.1 - 10.23.4.2.1 Method 1: From 1-(3-Pyridyl)-1H-benzotriazoles [Seite 376]
8.4.2.2 - 10.23.4.2.2 Method 2: From 2-Alkoxypyrano[3,2-b]indoles and Hydroxylamine [Seite 376]
8.4.3 - 10.23.4.3 Aromatization [Seite 377]
8.4.4 - 10.23.4.4 Synthesis by Substituent Modification [Seite 379]
8.4.4.1 - 10.23.4.4.1 Substitution of Existing Substituents [Seite 379]
8.4.4.1.1 - 10.23.4.4.1.1 Substitution of N-Hydrogen [Seite 379]
8.4.4.1.1.1 - 10.23.4.4.1.1.1 Giving N-Carbon 5H-Pyrido[3,2-b]indoles [Seite 379]
8.4.4.1.1.1.1 - 10.23.4.4.1.1.1.1 Method 1: Using an Alkyl Halide and Sodium Hydride [Seite 379]
8.4.4.1.1.1.2 - 10.23.4.4.1.1.1.2 Method 2: Demethylation of a 1-Methyl-5H-pyrido[3,2-b]indol-1-ium Iodide [Seite 380]
8.4.4.1.1.1.3 - 10.23.4.4.1.1.1.3 Method 3: 5-Arylation Using an Aryl Halide [Seite 383]
8.4.4.1.2 - 10.23.4.4.1.2 Substitution of C-Hydrogen [Seite 384]
8.4.4.1.2.1 - 10.23.4.4.1.2.1 Substitution by Electrophiles [Seite 384]
8.4.4.1.2.1.1 - 10.23.4.4.1.2.1.1 Method 1: Giving C-Nitrogen 5H-Pyrido[3,2-b]indoles [Seite 384]
8.4.4.1.2.2 - 10.23.4.4.1.2.2 Substitution via Metalation [Seite 385]
8.4.4.2 - 10.23.4.4.2 Modification of Substituents [Seite 386]
8.4.4.2.1 - 10.23.4.4.2.1 Modification of C-Carbon Functionalities [Seite 386]
8.4.4.2.1.1 - 10.23.4.4.2.1.1 Method 1: Giving C-Nitrogen 5H-Pyrido[3,2-b]indoles [Seite 386]
8.4.4.2.1.2 - 10.23.4.4.2.1.2 Method 2: Giving C-Carbon 5H-Pyrido[3,2-b]indoles [Seite 386]
9 - 30.3 Product Class 3: S, S-Acetals [Seite 401]
10 - 30.3.2.2 1,3-Dithietanes [Seite 415]
10.1 - 30.3.2.2.1 Symmetrical Dithietanes [Seite 415]
10.1.1 - 30.3.2.2.1.1 Method 1: Dimerization of Thioketones Formed In Situ from Bunte Salts [Seite 415]
10.1.2 - 30.3.2.2.1.2 Method 2: Synthesis from Thiophosgene: Dimerization of Thiocarbonates [Seite 416]
10.1.3 - 30.3.2.2.1.3 Method 3: Dimerization of Thioacetamides [Seite 417]
10.2 - 30.3.2.2.2 Unsymmetrical Dithietanes [Seite 417]
10.2.1 - 30.3.2.2.2.1 Method 1: Synthesis from Thioketones and Imines [Seite 417]
10.2.2 - 30.3.2.2.2.2 Method 2: Synthesis from Aromatic Aldehydes and Carbon Disulfide [Seite 418]
10.2.3 - 30.3.2.2.2.3 Method 3: Synthesis of Dithietane Cations [Seite 419]
11 - 30.3.3.2 1,3-Dithiolanes [Seite 421]
11.1 - 30.3.3.2.1 Method 1: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Protic Acids [Seite 421]
11.1.1 - 30.3.3.2.1.1 Variation 1: Catalyzed by Hydrogen Chloride [Seite 421]
11.1.2 - 30.3.3.2.1.2 Variation 2: Catalyzed by 4-Toluenesulfonic Acid [Seite 422]
11.1.3 - 30.3.3.2.1.3 Variation 3: Catalyzed by Sulfuric Acid on Silica Gel [Seite 422]
11.1.4 - 30.3.3.2.1.4 Variation 4: Catalyzed by Alumina Sulfuric Acid, Silica Sulfuric Acid, and Tungstate Sulfuric Acid [Seite 423]
11.1.5 - 30.3.3.2.1.5 Variation 5: Catalyzed by Sulfamic Acid on Silica Gel [Seite 427]
11.1.6 - 30.3.3.2.1.6 Variation 6: Catalyzed by Sulfonic Acids on Solid Supports and Ionic Liquids [Seite 428]
11.1.7 - 30.3.3.2.1.7 Variation 7: Catalyzed by Sodium Hydrogen Sulfate on Silica Gel [Seite 431]
11.1.8 - 30.3.3.2.1.8 Variation 8: Catalyzed by Solid-Supported Perchloric Acid [Seite 432]
11.1.9 - 30.3.3.2.1.9 Variation 9: Catalyzed by Trichloroacetic Acid in Sodium Dodecyl Sulfate Micelles [Seite 432]
11.2 - 30.3.3.2.2 Method 2: Reactions of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Lewis Acids [Seite 433]
11.2.1 - 30.3.3.2.2.1 Variation 1: Catalyzed by Boron-Based Reagents [Seite 433]
11.2.2 - 30.3.3.2.2.2 Variation 2: Catalyzed by Aluminum Chloride and Related Reagents [Seite 435]
11.2.3 - 30.3.3.2.2.3 Variation 3: Catalyzed by Indium(III) Reagents [Seite 437]
11.2.4 - 30.3.3.2.2.4 Variation 4: Catalyzed by Silicon-Based Reagents [Seite 439]
11.2.5 - 30.3.3.2.2.5 Variation 5: Catalyzed by Tin-Based Reagents [Seite 440]
11.2.6 - 30.3.3.2.2.6 Variation 6: Catalyzed by Titanium-Based Reagents [Seite 441]
11.2.7 - 30.3.3.2.2.7 Variation 7: Catalyzed by Vanadium-Based Reagents [Seite 442]
11.2.8 - 30.3.3.2.2.8 Variation 8: Catalyzed by Iron-Based Reagents [Seite 444]
11.2.9 - 30.3.3.2.2.9 Variation 9: Catalyzed by Ruthenium-Based Reagents [Seite 446]
11.2.10 - 30.3.3.2.2.10 Variation 10: Catalyzed by Nickel-Based Reagents [Seite 448]
11.2.11 - 30.3.3.2.2.11 Variation 11: Promoted by Copper-Based Reagents [Seite 449]
11.2.12 - 30.3.3.2.2.12 Variation 12: Catalyzed by Zinc-Based Reagents [Seite 450]
11.2.13 - 30.3.3.2.2.13 Variation 13: Catalyzed by Hafnium-Based Reagents [Seite 451]
11.3 - 30.3.3.2.3 Method 3: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Heterogeneous Catalysts [Seite 452]
11.3.1 - 30.3.3.2.3.1 Variation 1: Catalyzed by Phosphorus Pentoxide on Alumina and Silica Gel Reagents [Seite 452]
11.3.2 - 30.3.3.2.3.2 Variation 2: Using Dithiolanylium Tetrafluoroborate Salts on Solid Support [Seite 455]
11.3.3 - 30.3.3.2.3.3 Variation 3: Catalyzed by Graphene Oxide [Seite 456]
11.4 - 30.3.3.2.4 Method 4: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Halogens and Derivatives [Seite 457]
11.4.1 - 30.3.3.2.4.1 Variation 1: Catalyzed by Iodine [Seite 457]
11.4.2 - 30.3.3.2.4.2 Variation 2: Catalyzed by Tribromide Salts [Seite 459]
11.4.3 - 30.3.3.2.4.3 Variation 3: Catalyzed by N-Bromosuccinimide [Seite 461]
11.4.4 - 30.3.3.2.4.4 Variation 4: Catalyzed by Poly(N-bromoacrylamide) [Seite 462]
11.4.5 - 30.3.3.2.4.5 Variation 5: Catalyzed by N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide and Poly(ethylene-N,N'-dibromobenzene-1,3-disulfonamide) [Seite 463]
11.4.6 - 30.3.3.2.4.6 Variation 6: Catalyzed by Trichloromelamine [Seite 464]
11.5 - 30.3.3.2.5 Method 5: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Ionic Liquids [Seite 465]
11.5.1 - 30.3.3.2.5.1 Variation 1: Catalyzed by Iminium Salts Structurally Similar to Ionic Liquids [Seite 465]
11.6 - 30.3.3.2.6 Method 6: Reaction of Ethane-1,2-dithiol with Masked Carbonyl Groups [Seite 467]
11.6.1 - 30.3.3.2.6.1 Variation 1: Conversion of (E)-2-Chlorovinyl Sulfones into 1,3-Dithiolane Derivatives [Seite 467]
11.6.2 - 30.3.3.2.6.2 Variation 2: One-Pot Conversion of Ethoxyacetylene, an a,ß-Unsaturated Aldehyde, and Ethane-1,2-dithiol into a 2-(Buta-1,3-dienyl)-1,3-dithiolane [Seite 467]
11.7 - 30.3.3.2.7 Method 7: Reaction of O,O-Acetals or Hemiacetals with Ethane-1,2-dithiol [Seite 468]
11.7.1 - 30.3.3.2.7.1 Variation 1: Catalyzed by Protic Acids [Seite 468]
11.7.2 - 30.3.3.2.7.2 Variation 2: Catalyzed by Lewis Acids [Seite 471]
11.7.3 - 30.3.3.2.7.3 Variation 3: Catalyzed by Heterogeneous Catalysts [Seite 473]
11.7.4 - 30.3.3.2.7.4 Variation 4: Catalyzed by Halogens and Derivatives [Seite 474]
11.8 - 30.3.3.2.8 Method 8: Dithioacetalization from a 1,3-Dithiolane to Another Carbonyl Group [Seite 476]
11.9 - 30.3.3.2.9 Method 9: Addition of Ethane-1,2-dithiol to Alkynes [Seite 477]
11.9.1 - 30.3.3.2.9.1 Variation 1: Gold(I)/Silver(I) Tetrafluoroborate Catalyzed Bishydrothiolation of Alkynes [Seite 477]
11.9.2 - 30.3.3.2.9.2 Variation 2: Calcium Nonafluorobutane-1-sulfonate Catalyzed anti-Markovnikov Bishydrothiolation of Alkynes [Seite 477]
11.9.3 - 30.3.3.2.9.3 Variation 3: Double Michael Addition of Ethane-1,2-dithiol to Propargylic Carbonyl Systems [Seite 478]
11.10 - 30.3.3.2.10 Method 10: Metalation [Seite 481]
11.10.1 - 30.3.3.2.10.1 Variation 1: 2-(Trimethylsilyl)-1,3-dithiolanes as Masked 1,3-Dithiolane Anions [Seite 482]
11.11 - 30.3.3.2.11 Method 11: Annulation [Seite 483]
11.11.1 - 30.3.3.2.11.1 Variation 1: Tandem Hydride Shift/Cyclization [Seite 483]
11.11.2 - 30.3.3.2.11.2 Variation 2: [6 + 3] Cycloaddition [Seite 484]
11.11.3 - 30.3.3.2.11.3 Variation 3: [4 + 2] Cycloaddition [Seite 485]
11.12 - 30.3.3.2.12 Method 12: Metal-Free Cross-Dehydrogenative Coupling of 1H-Benzimidazoles with 1,3-Dithiolane [Seite 486]
11.13 - 30.3.3.2.13 Method 13: Reduction of Ketene S,S-Acetals [Seite 487]
11.14 - 30.3.3.2.14 Method 14: [3 + 2] Cycloaddition of Ketene S,S-Acetals [Seite 488]
11.15 - 30.3.3.2.15 Method 15: Intramolecular Cyclization of Ketene S,S-Acetals [Seite 489]
11.15.1 - 30.3.3.2.15.1 Variation 1: Nazarov Cyclization-Halovinylation of a-Alkenoyl Ketene S,S-Acetals [Seite 489]
11.15.2 - 30.3.3.2.15.2 Variation 2: Intramolecular Michael Reaction [Seite 490]
11.16 - 30.3.3.2.16 Method 16: Double-Bond Migration in Ketene S,S-Acetals [Seite 491]
12 - Author Index [Seite 497]
13 - Abbreviations [Seite 517]
