Foreword ..................................................... viii
Preface ........................................................ ix
Contributing Authors ........................................... xi
PART 1 THREE- AND FOUR-MEMBERED HETEROCYCLES ................... 1
Chapter 1 Aziridines and Epoxides .............................. 1
1.1 Blum Aziridine Synthesis ................................... 2
1.2 Gabriel-Heine Aziridine Isomerization ..................... 11
1.3 Shi Epoxidation ........................................... 21
PART 2 FIVE-MEMBERED HETEROCYCLES .............................. 41
Chapter 2 Pyrroles and Pyrrolidines ........................... 41
2.1 Clauson-Kass Pyrrole Synthesis ............................ 42
2.2 Houben-Hoesch Acylation of Pyrroles ....................... 53
2.3 Overman Pyrrolidine Synthesis ............................. 60
2.4 Trofimov Synthesis of Pyrroles ............................ 72
Chapter 3 Indoles .............................................. 83
3.1 Bischler-Möhlau Indole Synthesis .......................... 84
3.2 Borsche-Drechsel Cyclization .............................. 91
3.3 Buchwald-Hartwig Indole Synthesis ........................ 102
3.4 Cadogan-Sundberg Indole Synthesis ........................ 112
3.5 Fukuyama Indole Synthesis ................................ 125
3.6 Gassman Oxindole Synthesis ............................... 133
3.7 Larock Indole Synthesis .................................. 143
3.8 Matinet Dioxindole Reaction .............................. 167
3.9 Mori-Ban Indole Synthesis ................................ 175
3.10 Sandmeyer Isatin Synthesis ............................... 187
3.11 Sommelet-Hauser Rearrangement ............................ 197
3.12 Stollé Oxindole Synthesis ................................ 207
Chapter 4 Furans and Oxazoles ................................ 213
4.1 Nierenstein Reaction ..................................... 214
4.2 Davidson Oxazole Synthesis ............................... 221
4.3 Fischer Oxazole Synthesis ................................ 225
4.4 Japp Oxazole Synthesis ................................... 233
4.5 Schöllkopf Oxazole Synthesis ............................. 242
Chapter 5 Other Five-Membered Heterocycles .................... 259
5.1 Bamberger Imidazole Cleavage ............................. 260
5.2 Dimroth Triazole Synthesis ............................... 269
5.3 Finnegan Tetrazole Synthesis ............................. 278
5.4 Hantzsch Thiazole Synthesis .............................. 299
5.5 Huisgen Tetrazole Rearrangement .......................... 309
5.6 Knorr Pyrazole Synthesis ................................. 317
5.7 Pechmann Pyrazole Synthesis .............................. 327
PART 3 SIX-MEMBERED HETEROCYCLES ............................. 337
Chapter 6 Pyridines .......................................... 337
6.1 Baeyer Pyridine Synthesis ................................ 338
6.2 Katrizky Pyridine Synthesis .............................. 347
Chapter 7 Quinolines and Isoquinolines ........................ 351
7.1 Betti Reaction ........................................... 352
7.2 Bernthsen Acridine Synthesis ............................. 360
7.3 Lehmstedt-Tănăsescu Reaction ............................. 368
7.4 Niementowski Quinoline Synthesis ......................... 376
7.5 Povarov Reaction ......................................... 385
Chapter 8 Six-Membered Heterocycles .......................... 401
8.1 Balaban-Nenitzescu-Praill Reaction ....................... 402
8.2 Borsche Cinnoline Synthesis .............................. 420
8.3 Gutknecht Pyrazine Synthesis ............................. 430
8.4 Niementowski Quinazoline Synthesis ....................... 440
8.5 Pechmann Coumarin Synthesis .............................. 454
8.6 Robinson-Schöpf Condensation ............................. 470
8.7 Simonis Chromone Cyclization ............................. 477
8.8 Wesseley-Moser Rearrangement ............................. 487
8.9 Widman-Stoermer Cinnoline Synthesis ...................... 493
8.10 Wichterle Reaction ....................................... 497
Chapter 9 Miscellaneous Name Reactions ....................... 515
9.1 ANRORC Mechanism ......................................... 516
9.2 Boulton-Katritzky Rearrangement .......................... 527
9.3 Chichibabin Amination Reaction ........................... 539
9.4 Dimroth Rearrangement .................................... 554
9.5 Hantzsch Synthesis ....................................... 591
9.6 Ortoleva-King Reaction ................................... 645
9.1 Appendixes
Appendix 1 Table of Contents for Volume 1: Name Reactions
in Heterocyclic Chemistry ................................ 651
Appendix 2 Table of Contents for Volume 2: Name Reactions
for Functional Group Transformations ..................... 655
Appendix 3 Table of Contents for Volume 3: Name Reactions
for Homologations-I ...................................... 657
Appendix 4 Table of Contents for Volume 4: Name Reactions
for Homologations-II ..................................... 659
Appendix 5 Table of Contents for Volume 5: Name Reactions
for Ring Formations ...................................... 661
Subject Index ................................................. 663
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