Name Reactions in Heterocyclic Chemistry
1st Edition
Published on 2. November 2004
Book
Hardback
592 pages
978-0-471-30215-5 (ISBN)
Description
Covers important name reactions relevant to heterocyclic chemistry The field of heterocyclic chemistry has long presented a special challenge for chemists. Because of the enormous amount and variety of information, it is often a difficult topic to cover for undergraduate and graduate chemistry students, even in simplified form. Yet the chemistry of heterocyclic compounds and methods for their synthesis form the bedrock of modern medicinal chemical and pharmaceutical research. Thus there is a great need for high quality, up-to-date, and authoritative books on heterocyclic synthesis helpful to both the professional research chemist as well as the advanced student.
Name Reactions in Heterocyclic Chemistry provides a one-stop repository for this important field of organic chemistry. The primary topics include three- and four-membered heterocycles, five-membered heterocycles including indoles, furans, thiophenes, and oxazoles, six-membered heterocycles including quinolines, isoquinolines, and pyrimidines, and other heterocycles.
Each name reaction is summarized in seven sections:
Description
Historical perspective
Mechanism
Variations and improvements
Synthetic utility
Experimental
References
Authored by a team of world-renowned contributors - some of whom have discovered the very reactions they describe - Name Reactions in Heterocyclic Chemistry represents a state-of-the-art resource for students and researchers alike.
Name Reactions in Heterocyclic Chemistry provides a one-stop repository for this important field of organic chemistry. The primary topics include three- and four-membered heterocycles, five-membered heterocycles including indoles, furans, thiophenes, and oxazoles, six-membered heterocycles including quinolines, isoquinolines, and pyrimidines, and other heterocycles.
Each name reaction is summarized in seven sections:
Description
Historical perspective
Mechanism
Variations and improvements
Synthetic utility
Experimental
References
Authored by a team of world-renowned contributors - some of whom have discovered the very reactions they describe - Name Reactions in Heterocyclic Chemistry represents a state-of-the-art resource for students and researchers alike.
Reviews / Votes
"...is not only an indispensable resource for senior undergraduate and graduate students....but also a good reference for all chemists interested in the chemistry of heterocyclic compounds..." (Drug Development and Industrial Pharmacy, No. 10, 2005) "...a major contribution to the field and is highly recommended." (Journal of Medicinal Chemistry, June 30, 2005)More details
Series
Language
English
Place of publication
United States
Publishing group
John Wiley & Sons Inc
Target group
Professional and scholarly
Product notice
sewn/stitched
Cloth over boards
Dimensions
Height: 236 mm
Width: 193 mm
Thickness: 33 mm
Weight
1134 gr
ISBN-13
978-0-471-30215-5 (9780471302155)
Copyright in bibliographic data and cover images is held by Nielsen Book Services Limited or by the publishers or by their respective licensors: all rights reserved.
Schweitzer Classification
Other editions
Additional editions
Jie Jack Li
Name Reactions in Heterocyclic Chemistry
E-Book
12/2004
Wiley
€206.99
Available for download
Person
JIE JACK LI is a medicinal chemist at Pf izer Global Research and Development in Ann Arbor, Michigan. His research interests include medicinal chemistry, heterocyclic chemistry, transition metal-catalyzed reactions, and radical chemistry. He is author of Name Reactions: A Collection of Detailed Reaction Mechanisms, and coauthor of Palladium in Heterocyclic Chemistry and Contemporary Drug Synthesis, also published by Wiley.
Content
Foreword x
Preface xi
Acronyms and abbreviations xiv
Part 1 Three- And Four-Membered Heterocycles 1
Chapter 1 Epoxides and Aziridines 1
1.1 Corey-Chaykovsky reaction 2
1.2 Darzens glycidic ester condensation 15
1.3 Hoch-Campbell aziridine synthesis 22
1.4 Jacobsen-Katsuki epoxidation 29
1.5 Paterno-Buechi reaction 44
1.6 Sharpless-Katsuki epoxidation 50
1.7 Wenker aziridine synthesis 63
Part 2 Five-Membered Heterocycles 69
Chapter 2 Pyrroles and Pyrrolidines 69
2.1 Barton-Zard reaction 70
2.2 Knorr and Paal-Knorr pyrrole syntheses 79
2.3 Hofmann-Loeffler-Freytag reaguo 90
Chapter 3 Indoles 99
3.1 Bartoli indole synthesis 100
3.2 Batcho-Leimgruber indole synthesis 104
3.3 Bucherer carbazole synthesis 110
3.4 Fischer indole synthesis 116
3.5 Gassman indole synthesis 128
3.6 Graebe-Ullman carbazole synthesis 132
3.7 Hegedus indole synthesis 135
3.8 Madelung indole synthesis 140
3.9 Nenitzescu indole synthesis 145
3.10 Reissert indole synthesis 154
Chapter 4 Furans
4.1 Feist-Benary furan synthesis 160
4.2 Paal-Knorr furan synthesis 168
Chapter 5 Thiophenes 183
5.1 Fiesselmann thiophene synthesis 184
5.2 Gewald aminothiophene synthesis 193
5.3 Hinsberg synthesis of thiophene derivatives 199
5.4 Paal thiophene synthesis 207
Chapter 6 Oxazoles and Isoxazoles 219
6.1 Claisen isoxazole synthesis 220
6.2 Cornforth rearrangement 225
6.3 Erlenmeyer-Ploechl azlactone synthesis 229
6.4 Fischer oxazole synthesis 234
6.5 Meyers oxazoline method 237
6.6 Robinson-Gabriel synthesis 249
6.7 van Leusen oxazole Synthesis 254
Chapter 7 Other Five-Membered Heterocycles 261
7.1 Auwers flavone synthesis 262
7.2 Bucherer-Bergs reaction 266
7.3 Cook-Heilbron 5-amino-thiazole synthesis 275
7.4 Hurd-Mori 1,2,3-thiadiazole synthesis 284
7.5 Knorr pyrazole synthesis 392
Part 3 Six-Membered Heterocycles 301
Chapter 8 Pyridines 302
8.1 Preparation via condensation reactions 303
8.1.1 Hantzsch (dihydro)-pyridine synthesis 304
8.1.1.1 Description 304
8.1.1.2 Historical perspective 304
8.1.1.3 Mechanism 305
8.1.1.4 Variations 307
8.1.1.4.1 Guareschi-Thorpe pyridine synthesis 307
8.1.1.4.2 Chichibabin (Tschitschibabin) pyridine synthesis 308
8.1.1.4.3 Bohlmann-Rahtz pyridine synthesis 309
8.1.1.4.4 Kroehnke pyridine synthesis 311
8.1.1.4.5 Petrenko-Kritschenko piperidone synthesis 313
8.1.1.5 Improvement or modifications 314
8.1.1.6 Experimental 320
8.1.1.6.1 Three-component coupling 320
8.1.1.6.2 Two-component coupling 320
8.1.1.7 References 321
8.2 Preparation via cycloaddition reactions 323
8.2.1 Boger reaction 323
8.3 Preparation via rearrangement reactions 340
8.3.1 Boekelheide reaction 340
8.3.2 Ciamician-Dennstedt rearrangement 350
8.4 Zincke reaction 355
Chapter 9 Quinolines and Isoquinolines 375
9.1 Bischler-Napieralski reaction 376
9.2 Camps quinoline synthesis 386
9.3 Combes quinoline synthesis 390
9.4 Conrad-Limpach reaction 398
9.5 Doebner quinoline synthesis 407
9.6 Friedlaender synthesis 411
9.7 Gabriel-Colman rearrangement 416
9.8 Gould-Jacobs reaction 423
9.9 Knorr quinoline synthesis 437
9.10 Meth-Cohn quinoline synthesis 443
9.11 Pfitzinger quinoline synthesis 451
9.12 Pictet-Gams isoquinoline synthesis 457
9.13 Pictet-Hubert reaction 465
9.14 Pictet-Spengler isoquinoline synthesis 469
9.15 Pomeranz-Fritsch reaction 480
9.16 Riehm quinoline synthesis 487
9.17 Skraup/Doebner-von Miller reaction 488
Chapter 10 Other Six-Membered Heterocycles
10.1 Algar-Flynn-Oyamada reaction 496
10.2 Beirut reaction 504
10.3 Biginelli reaction 509
10.4 Kostanecki-Robinson reaction 521
10.5 Pinner pyrimidine synthesis 536
10.6 von Richter cinnoline reaction 540
Subject Index 545
Preface xi
Acronyms and abbreviations xiv
Part 1 Three- And Four-Membered Heterocycles 1
Chapter 1 Epoxides and Aziridines 1
1.1 Corey-Chaykovsky reaction 2
1.2 Darzens glycidic ester condensation 15
1.3 Hoch-Campbell aziridine synthesis 22
1.4 Jacobsen-Katsuki epoxidation 29
1.5 Paterno-Buechi reaction 44
1.6 Sharpless-Katsuki epoxidation 50
1.7 Wenker aziridine synthesis 63
Part 2 Five-Membered Heterocycles 69
Chapter 2 Pyrroles and Pyrrolidines 69
2.1 Barton-Zard reaction 70
2.2 Knorr and Paal-Knorr pyrrole syntheses 79
2.3 Hofmann-Loeffler-Freytag reaguo 90
Chapter 3 Indoles 99
3.1 Bartoli indole synthesis 100
3.2 Batcho-Leimgruber indole synthesis 104
3.3 Bucherer carbazole synthesis 110
3.4 Fischer indole synthesis 116
3.5 Gassman indole synthesis 128
3.6 Graebe-Ullman carbazole synthesis 132
3.7 Hegedus indole synthesis 135
3.8 Madelung indole synthesis 140
3.9 Nenitzescu indole synthesis 145
3.10 Reissert indole synthesis 154
Chapter 4 Furans
4.1 Feist-Benary furan synthesis 160
4.2 Paal-Knorr furan synthesis 168
Chapter 5 Thiophenes 183
5.1 Fiesselmann thiophene synthesis 184
5.2 Gewald aminothiophene synthesis 193
5.3 Hinsberg synthesis of thiophene derivatives 199
5.4 Paal thiophene synthesis 207
Chapter 6 Oxazoles and Isoxazoles 219
6.1 Claisen isoxazole synthesis 220
6.2 Cornforth rearrangement 225
6.3 Erlenmeyer-Ploechl azlactone synthesis 229
6.4 Fischer oxazole synthesis 234
6.5 Meyers oxazoline method 237
6.6 Robinson-Gabriel synthesis 249
6.7 van Leusen oxazole Synthesis 254
Chapter 7 Other Five-Membered Heterocycles 261
7.1 Auwers flavone synthesis 262
7.2 Bucherer-Bergs reaction 266
7.3 Cook-Heilbron 5-amino-thiazole synthesis 275
7.4 Hurd-Mori 1,2,3-thiadiazole synthesis 284
7.5 Knorr pyrazole synthesis 392
Part 3 Six-Membered Heterocycles 301
Chapter 8 Pyridines 302
8.1 Preparation via condensation reactions 303
8.1.1 Hantzsch (dihydro)-pyridine synthesis 304
8.1.1.1 Description 304
8.1.1.2 Historical perspective 304
8.1.1.3 Mechanism 305
8.1.1.4 Variations 307
8.1.1.4.1 Guareschi-Thorpe pyridine synthesis 307
8.1.1.4.2 Chichibabin (Tschitschibabin) pyridine synthesis 308
8.1.1.4.3 Bohlmann-Rahtz pyridine synthesis 309
8.1.1.4.4 Kroehnke pyridine synthesis 311
8.1.1.4.5 Petrenko-Kritschenko piperidone synthesis 313
8.1.1.5 Improvement or modifications 314
8.1.1.6 Experimental 320
8.1.1.6.1 Three-component coupling 320
8.1.1.6.2 Two-component coupling 320
8.1.1.7 References 321
8.2 Preparation via cycloaddition reactions 323
8.2.1 Boger reaction 323
8.3 Preparation via rearrangement reactions 340
8.3.1 Boekelheide reaction 340
8.3.2 Ciamician-Dennstedt rearrangement 350
8.4 Zincke reaction 355
Chapter 9 Quinolines and Isoquinolines 375
9.1 Bischler-Napieralski reaction 376
9.2 Camps quinoline synthesis 386
9.3 Combes quinoline synthesis 390
9.4 Conrad-Limpach reaction 398
9.5 Doebner quinoline synthesis 407
9.6 Friedlaender synthesis 411
9.7 Gabriel-Colman rearrangement 416
9.8 Gould-Jacobs reaction 423
9.9 Knorr quinoline synthesis 437
9.10 Meth-Cohn quinoline synthesis 443
9.11 Pfitzinger quinoline synthesis 451
9.12 Pictet-Gams isoquinoline synthesis 457
9.13 Pictet-Hubert reaction 465
9.14 Pictet-Spengler isoquinoline synthesis 469
9.15 Pomeranz-Fritsch reaction 480
9.16 Riehm quinoline synthesis 487
9.17 Skraup/Doebner-von Miller reaction 488
Chapter 10 Other Six-Membered Heterocycles
10.1 Algar-Flynn-Oyamada reaction 496
10.2 Beirut reaction 504
10.3 Biginelli reaction 509
10.4 Kostanecki-Robinson reaction 521
10.5 Pinner pyrimidine synthesis 536
10.6 von Richter cinnoline reaction 540
Subject Index 545