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Progress in Heterocyclic Chemistry
     

Progress in Heterocyclic Chemistry

5.0 3
by Gordon W. Gribble
 

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ISBN-10: 0080968058

ISBN-13: 9780080968056

Pub. Date: 11/21/2011

Publisher: Elsevier Science

Progress in Heterocyclic Chemistry (PHC), is an annual review series commissioned by the International Society of Heterocyclic Chemistry (ISHC). Volumes in the series contain both highlights of the previous year's literature on heterocyclic chemistry and articles on new developing topics of particular interest to heterocyclic chemists. The highlight chapters in Volume

Overview

Progress in Heterocyclic Chemistry (PHC), is an annual review series commissioned by the International Society of Heterocyclic Chemistry (ISHC). Volumes in the series contain both highlights of the previous year's literature on heterocyclic chemistry and articles on new developing topics of particular interest to heterocyclic chemists. The highlight chapters in Volume 20 are all written by leading researchers in their field and these chapters constitute a systematic survey of the important original material reported in the literature of heterocyclic chemistry in 2007. Additional articles in this volume review '2-Indolylacyl radicals in the synthesis of indole compounds' and 'Cascade reactions of carbonyl ylides for heterocyclic synthesis'.

Product Details

ISBN-13:
9780080968056
Publisher:
Elsevier Science
Publication date:
11/21/2011
Series:
Progress in Heterocyclic Chemistry Series , #23
Pages:
550
Product dimensions:
5.90(w) x 9.10(h) x 1.30(d)

Table of Contents

Foreword x

Editorial Advisory Board Members xi

Chapter 1 2-Indolylacyl radicals in the synthesis of indole compounds M.-Lluisa Bennasar Tomas Roca 1

1.1 Introduction 1

1.2 Radical reactions in synthesis: a short overview 1

1.3 2-Indolylacyl radicals: intermolecular and cascade reactions 2

1.3.1 Intermolecular addition reactions 2

1.3.2 Intermolecular addition-indole cyclisation cascade reactions 3

1.4 Intramolecular reactions of 2-indolylacyl radicals with alkenes 4

1.4.1 Cyclization of 5-hexenoyl radicals. Total synthesis of ([plus or minus])-guatambuine 5

1.4.2 Cyclization of 6-heptenoyl radicals 7

1.4.3 Cyclization of 7-octenoyl radicals 9

1.5 Intramolecular reactions of 2-indolylacyl radicals with aromatic and heteroaromatic systems 11

1.5.1 Cyclization upon benzenes 11

1.5.2 Cyclization upon pyridines 13

1.5.3 Cyclization upon quinolines. Synthesis of calothrixin B 14

1.6 Conclusion 16

1.7 Acknowledgments 16

1.8 References 16

Chapter 2 Cascade reactions of carbonyl ylides for heterocyclic synthesis Albert Padwa 20

2.1 Introduction 20

2.2 Carbonyl ylide cycloadditions 21

2.2.1 Intramolecular carbenoid-carbonyl cyclization sequence 21

2.2.2 Application of the method toward complex tetrahydrofuranyl natural products 22

2.2.3 Isomunchnone cycloadditions 29

2.2.4 Intramolecular isomunchnone cycloadditions 33

2.2.5 Cyclization-cycloaddition-cationic [pi]-cyclization reactions 35

2.2.6 Cycloadditions across heteroaromatic [pi]-systems 39

2.2.7 Push-pull carbonyl ylide cycloadditions 41

2.3 Conclusion 44

2.4 Acknowledgments 44

2.5 References 44

Chapter 3 Three-membered ring systems Stephen C. Bergmeier David J. Lapinsky47

3.1 Introduction 47

3.2 Epoxides 47

3.2.1 Preparation of epoxides 47

3.2.2 Reactions of epoxides 53

3.3 Aziridines 60

3.3.1 Preparation of aziridines 60

3.3.2 Reactions of aziridines 67

3.4 References 70

Chapter 4 Four-membered ring systems Benito Alcaide Pedro Almendros 74

4.1 Introduction 74

4.2 Azetidines, 3-azetidinones, and diazetines 74

4.3 Monocyclic 2-azetidinones ([beta]-lactams) 77

4.4 Fused and spirocyclic [beta]-lactams 81

4.5 Oxetanes, dioxetanes, oxetanediones and 2-oxetanones ([beta]-lactones) 82

4.6 Thietanes, [beta]-sultams, and related systems 85

4.7 Silicon and phosphorus heterocycles. miscellaneous 86

4.8 References 88

Chapter 5 Five-membered ring systems

Part 1 Thiophenes and Se/Te analogs Tomasz Janosik Jan Bergman 94

5.1.1 Introduction 94

5.1.2 Thiophene ring synthesis 94

5.1.3 Reactions of thiophenes 98

5.1.4 Non-polymeric thiophene organic materials 104

5.1.5 Thiophene oligomers and polymers 106

5.1.6 Thiophene derivatives in medicinal chemistry 111

5.1.7 Selenophenes and tellurophenes 113

5.1.8 References 115

Part 2 Pyrroles and benzo analogs Jonathon S. Russel Erin T. Pelkey 122

5.2.1 Introduction 122

5.2.2 Synthesis of pyrroles 122

5.2.2.1 Intramolecular approaches to pyrroles 122

5.2.2.2 Intermolecular approaches to pyrroles 124

5.2.2.3 Transformations of heterocycles and carbocycles to pyrroles 127

5.2.3 Reactions of pyrroles 128

5.2.3.1 Substitutions at pyrrole nitrogen 128

5.2.3.2 Substitution at pyrrole carbon 129

5.2.3.3 Functionalization of the side-chain 131

5.2.3.4 Transformations of pyrroles to other heterocycles 131

5.2.4 Pyrrole natural products and materials 132

5.2.4.1 Pyrrole natural products 132

5.2.4.2 Pyrrole materials 133

5.2.5 Synthesis of indoles 133

5.2.5.1 Intramolecular approaches 134

5.2.5.2 Intermolecular approaches 137

5.2.6 Reactions of indoles 138

5.2.6.1 Pericyclic transformations 138

5.2.6.2 Substitution and C-2/C-3 138

5.2.6.3 Substitution at nitrogen 140

5.2.6.4 Functionalization of the benzene ring 140

5.2.7 Carbazoles and azaindoles 141

5.2.7.1 Carbazole natural products and ring synthesis 141

5.2.7.2 Azaindole ring synthesis 141

5.2.8 Indole natural products 141

5.2.8.1 Natural products isolation and characterization 141

5.2.8.2 Total synthesis: indole core and side-chain modifications 142

5.2.8.3 [beta]-Carbolines and tetrahydro-[beta]-carbolines 143

5.2.8.4 Oxindole and spirooxindole 144

5.2.9 Biochemical and medicinal chemistry 145

5.2.10 References 145

Part 3 Furans and benzofurans Xue-Long Hou Zhen Yang Kap-Sun Yeung Henry N. C. Wong 152

5.3.1 Introduction 152

5.3.2 Reactions 153

5.3.2.1 Furans 153

5.3.2.2 Di- and tetrahydrofurans 157

5.3.3 Synthesis 159

5.3.3.1 Furans 159

5.3.3.2 Di- and tetrahydrofurans 165

5.3.3.3 Benzo[b]furans and related compounds 172

5.3.3.4 Benzo[c]furans and related compounds 178

5.3.4 References 181

Part 4 With more than one N atom Larry Yet 190

5.4.1 Introduction 190

5.4.2 Pyrazoles and ring-fused derivatives 190

5.4.3 Imidazoles and ring-fused derivatives 196

5.4.4 1,2,3-Triazoles and ring-fused derivatives 203

5.4.5 1,2,4-Triazoles and ring-fused derivatives 208

5.4.6 Tetrazoles and ring-fused derivatives 210

5.4.7 References 213

Part 5 With N and S (Se) atoms Yong-Jin Wu Bingwei V. Yang 220

5.5.1 Introduction 220

5.5.2 Thiazoles 220

5.5.2.1 Synthesis of thiazoles 220

5.5.2.2 Synthesis of fused thiazoles 223

5.5.2.3 Synthesis of thiazolines 226

5.5.2.4 Reactions of thiazoles and fused derivatives 228

5.5.2.5 Thiazole intermediates in synthesis 233

5.5.2.6 Thiazolium-catalyzed reactions 235

5.5.2.7 Synthesis of thiazole-containing natural products 236

5.5.2.8 New thiazole-containing natural products 237

5.5.2.9 Thiazole-containing drug candidates 238

5.5.3 Isothiazoles 239

5.5.3.1 Synthesis of isothiazoles 239

5.5.3.2 Reactions of isothiazoles 241

5.5.3.3 Isothiazoles as auxiliaries and reagents in organic syntheses 242

5.5.3.4 Pharmaceutically interesting isothiazoles 244

5.5.4 Thiadiazoles and selenodiazoles 245

5.5.5 1,3-Selenazoles, 1,3-selenadolidines and 1,3-tellurazoles 248

5.5.6 References 249

Part 6 With O and S (Se, Te) atoms R. Alan Aitken Lynn A. Power 253

5.6.1 1,3-Dioxoles and dioxolanes 253

5.6.2 1,3-Dithioles and dithiolanes 255

5.6.3 1,3-Oxathioles and oxathiolanes 259

5.6.4 1,2-Dioxolanes 260

5.6.5 1,2-Dithioles and dithiolanes 260

5.6.6 1,2-Oxathioles and oxathiolanes 261

5.6.7 Three heteroatoms 261

5.6.8 References 261

Part 7 With O and N atoms Stefano Cicchi Franca M. Cordero Donatella Giomi 265

5.7.1 Isoxazoles 265

5.7.2 Isoxazolines 268

5.7.3 Isoxazolidines 271

5.7.4 Oxazoles 274

5.7.5 Oxazolines 278

5.7.6 Oxazolidines 283

5.7.7 Oxadiazoles 284

5.7.8 References 285

Chapter 6 Six-membered ring systems

Part 1 Pyridines and benzo derivatives Darrin W. Hopper Kristina M.K. Kutterer Jeremy J. Clemens Aimee L. Crombie 289

6.1.1 Introduction 289

6.1.2 Pyridines 289

6.1.2.1 Preparation of pyridines 289

6.1.2.2 Reactions of pyridines 294

6.1.2.3 Pyridine N-oxides and pyridinium salts 299

6.1.3 Quinolines 302

6.1.3.1 Preparation of quinolines 302

6.1.3.2 Reactions of quinolines 306

6.1.4 Isoquinolines 308

6.1.4.1 Preparation of isoquinolines 308

6.1.4.2 Reactions of isoquinolines 310

6.1.5 Piperidines 311

6.1.5.1 Preparations of piperidines 311

6.1.6 References 321

Part 2 Diazines and benzo derivatives Amelia Manlove Michael P. Groziak 333

6.2.1 Introduction 333

6.2.2 Reviews and general studies 333

6.2.3 Pyridazines and benzo derivatives 334

6.2.3.1 Syntheses 335

6.2.3.2 Reactions 336

6.2.3.3 Applications 336

6.2.4 Pyrimidines and benzo derivatives 337

6.2.4.1 Syntheses 341

6.2.4.2 Reactions 345

6.2.4.3 Applications 346

6.2.5 Pyrazines and benzo derivatives 350

6.2.5.1 Syntheses 352

6.2.5.2 Reactions 353

6.2.5.3 Applications 353

6.2.6 References 355

Part 3 Triazines, tetrazines and fused ring polyaza systems 364

Part 4 With O and/or S atoms (2006) John D. Hepworth B. Mark Heron 365

6.4.1 Introduction 365

6.4.2 Heterocycles containing one oxygen atom 366

6.4.2.1 Pyrans 366

6.4.2.2 [1]Benzopyrans and dihydro[1]benzopyrans (chromenes and chromans) 369

6.4.2.3 [2]Benzopyrans and dihydro[2]benzopyrans (isochromenes and isochromans) 373

6.4.2.4 Pyranones 375

6.4.2.5 Coumarins 379

6.4.2.6 Chromones 382

6.4.2.7 Xanthones and xanthenes 385

6.4.3 Heterocycles containing one sulfur atom 385

6.4.3.1 Thiopyrans and analogues 385

6.4.4 Heterocycles containing two or more oxygen atoms 388

6.4.4.1 Dioxins and dioxanes 388

6.4.4.2 Trioxanes 390

6.4.4.3 Tetraoxanes 390

6.4.5 Heterocycles containing two or more sulfur atoms 390

6.4.5.1 Dithianes and trithianes 390

6.4.6 Heterocycles containing both oxygen and sulfur in the same ring 392

6.4.6.1 Oxathianes 392

6.4.7 References 393

Part 4 With O and/or S atoms (2007) John D. Hepworth B. Mark Heron 399

6.4.1 Introduction 399

6.4.2 Heterocycles containing one oxygen atom 401

6.4.2.1 Pyrans 401

6.4.2.2 [1]Benzopyrans and dihydro[1]benzopyrans (chromenes and chromans) 404

6.4.2.3 [2]Benzopyrans and dihydro[2]benzopyrans (isochromenes and isochromans) 409

6.4.2.4 Pyrylium salts 410

6.4.2.5 Pyranones 411

6.4.2.6 Coumarins 414

6.4.2.7 Chromones 417

6.4.2.8 Xanthones and xanthenes 419

6.4.3 Heterocycles containing one sulfur atom 421

6.4.3.1 Thiopyrans and analogues 421

6.4.4 Heterocycles containing two or more oxygen atoms 423

6.4.4.1 Dioxins and dioxanes 423

6.4.4.2 Trioxanes 424

6.4.5 Heterocycles containing two or more sulfur atoms 424

6.4.5.1 Dithianes and trithianes 424

6.4.6 Heterocycles containing both oxygen and sulfur in the same ring 425

6.4.6.1 Oxathianes 425

6.4.7 References 426

Chapter 7 Seven-membered rings Jason A. Smith John H. Ryan 432

7.1 Introduction 432

7.2 Seven-membered systems containing one heteroatom 432

7.2.1 Azepines and derivatives 432

7.2.2 Fused azepines and derivatives 435

7.2.3 Benzoazepines and derivatives 437

7.2.4 Oxepine and fused derivatives 437

7.2.5 Thiepine and fused derivatives 438

7.3 Seven-membered systems containing two heteroatoms 439

7.3.1 Diazepines and fused derivatives 439

7.3.2 Dioxepines, dithiepines and fused derivatives 446

7.3.3 Miscellaneous derivatives with two heteroatoms 447

7.4 Seven-membered systems containing three or more heteroatoms 448

7.4.1 Systems with N, S and/or O 448

7.5 Seven-membered systems of pharmacological significance 450

7.6 Future directions 453

7.7 References 453

Chapter 8 Eight-membered and larger rings George R. Newkome 459

8.1 Introduction 459

8.2 Carbon-oxygen rings 460

8.3 Carbon-nitrogen rings 462

8.4 Carbon-sulfur rings 464

8.5 Carbon-oxygen/carbon-nitrogen rings 465

8.6 Carbon-nitrogen-oxygen rings 466

8.7 Carbon-nitrogen-sulfur rings 468

8.8 Carbon-sulfur-oxygen rings 469

8.9 Carbon-nitrogen-sulfur-oxygen rings 470

8.10 Carbon-nitrogen-metal rings 470

8.11 Carbon-nitrogen-sulfur-metal rings 470

8.12 Carbon-phosphous-oxygen-metal rings 471

8.13 Carbon-nitrogen-phosphorus-sulfur-metal rings 472

8.14 References 472

Index 476

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