Name Reactions in Heterocyclic Chemistry II

by Jie Jack Li, E. J. Corey (Foreword by)

Overview

The up-to-DATE guide to name reactions in heterocyclic chemistry

Name Reactions in Heterocyclic Chemistry II presents a comprehensive treatise on name reactions in heterocyclic chemistry, one of the most exciting—and important—fields within organic chemistry today.

The book not only covers fresh ground, but also provides extensive information on new and/or expanded reactions in:

• Three- and four-membered heterocycles

• Five-membered heterocycles (pyrroles and pyrrolidines, indoles, furans, thiophenes, and oxazoles)

• Six-membered heterocycles, including pyridines, quinolines, and isoquinolines

Featuring contributions from the leading authorities in heterocyclic chemistry. Each section includes a description of the given reaction, as well as the relevant historical perspective, mechanism, variations and improvements, synthetic utilities, experimental details, and references to the current primary literature.

The reactions covered in Name Reactions in Heterocyclic Chemistry have been widely adopted in all areas of organic synthesis, from the medicinal/pharmaceutical field, to agriculture, to fine chemicals, and the book brings the most cutting-edge knowledge to practicing synthetic chemists and students, along with the tools needed to synthesize new and useful molecules.

Product Details

ISBN-13:	9780470085080
Publisher:	Wiley
Publication date:	09/13/2011
Series:	Comprehensive Name Reactions , #6
Pages:	704
Product dimensions:	7.60(w) x 9.30(h) x 1.60(d)

About the Author

Jie Jack Li is a Chemist at Bristol-Myers Squibb Company. He has authored or edited various books, including the first volume of Name Reactions in Heterocyclic Chemistry, Name Reactions for Functional Group Transformations, Name Reactions for Carbocyclic Ring Formations, and several others, all published by Wiley.

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Table of Contents

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 Stolle Oxindole Synthesis 207

Chapter 4 Furans and Ox azoles 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 Schhllkopf Oxazole Synthesis 242

Chapter 5 Other Five-Mem be red Heterocycles 259

5. L 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 Pyridincs 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 Bemthsen Acridine Synthesis 360

7.3 Lehmstedt-Tanasescu 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 Robin son-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 Animation Reaction 539

9.4 Dimroth Rearrangement 554

9.5 Hantzsch Synthesis 591

9.6 Ortolcva-King Reaction 645

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 Hornolegations-I 657

Appendix 4, Table of Contents for Volume 4; Name Reactions for Hornohgations-II 659

Appendix 5, Table of Contents for Volume 5: Name Reactions for Ring Formations 661

Subject Index 663