Name Reactions in Heterocyclic Chemistry
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.
1101205200
Name Reactions in Heterocyclic Chemistry
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.
254.95 In Stock
Name Reactions in Heterocyclic Chemistry

Name Reactions in Heterocyclic Chemistry

Name Reactions in Heterocyclic Chemistry

Name Reactions in Heterocyclic Chemistry

Overview

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.

Product Details

ISBN-13: 9780471302155
Publisher: Wiley
Publication date: 10/11/2004
Series: Comprehensive Name Reactions , #7
Pages: 592
Product dimensions: 7.80(w) x 9.30(h) x 1.40(d)

About the Author

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.

Table of Contents

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

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