Name Reactions in Heterocyclic Chemistry
Wiley-Interscience (Verlag)
978-0-471-30215-5 (ISBN)
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.
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.
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-Büchi 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-Löffler-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-Bénary 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-Plöchl 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 Kröhnke 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 Friedländer 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
| Erscheint lt. Verlag | 2.11.2004 |
|---|---|
| Reihe/Serie | Comprehensive Name Reactions |
| Sprache | englisch |
| Maße | 198 x 236 mm |
| Gewicht | 1179 g |
| Themenwelt | Naturwissenschaften ► Chemie ► Organische Chemie |
| ISBN-10 | 0-471-30215-5 / 0471302155 |
| ISBN-13 | 978-0-471-30215-5 / 9780471302155 |
| Zustand | Neuware |
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