Progress in Heterocyclic Chemistry (eBook)

Gordon Gribble, J. Joule (Herausgeber)

eBook Download: PDF

2009 | 1. Auflage
572 Seiten
Elsevier Science (Verlag)
978-0-08-096516-1 (ISBN)

Infos

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 emerging topics of particular interest to heterocyclic chemists. The chapters in Volume 21 constitute a systematic survey of the important original material reported in the literature of heterocyclic chemistry in 2008. Additional articles in this volume review 'Biocatalytic approaches to chiral heterocycles' and 'Ring-expanded ('fat') purines and their nucleoside/nucleotide analogues as broad-spectrum therapeutics.'

As with previous volumes in the series, Volume 21 apprises academic/industrial chemists and advanced students of developments in heterocyclic chemistry in a convenient format.

* Covers the heterocyclic literature published in 2008

* Includes specialized reviews

* Features contributions from leading researchers in their fields

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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 emerging topics of particular interest to heterocyclic chemists. The chapters in Volume 21 constitute a systematic survey of the important original material reported in the literature of heterocyclic chemistry in 2008. Additional articles in this volume review "e;Biocatalytic approaches to chiral heterocycles"e; and "e;Ring-expanded ('fat') purines and their nucleoside/nucleotide analogues as broad-spectrum therapeutics."e;As with previous volumes in the series, Volume 21 apprises academic/industrial chemists and advanced students of developments in heterocyclic chemistry in a convenient format. - Covers the heterocyclic literature published in 2008- Includes specialized reviews- Features contributions from leading researchers in their fields

Inhalt

Front Cover 1
Progress in Heterocyclic Chemistry 4
Copyright Page 5
Contents 6
Foreword 12
Chapter 1 Biocatalytic Approaches to Chiral Heterocycles 14
1.1 Introduction 14
1.2 Enzyme classes discussed 14
1.3 Three-membered ring systems 16
1.4. Four-membered ring systems 20
1.5 Five-membered ring systems 24
1.6 Six-membered ring systems 31
1.7 Seven-membered and larger ring systems 38
1.8 Conclusion 41
1.9 References 41
Chapter 2 Ring-Expanded (‘fat’) Purines and their Nucleoside/ Nucleotide Analogues as Broad-Spectrum Therapeutics 48
2.1 Introduction 48
2.2 Significance of ‘fat’ purines and their nucleoside/nucleotide analogues 48
2.3 Chemistry 52
2.4 Biochemical and biophysical chemistry 61
2.5 Biological activity 71
2.6 Conclusion 76
2.7 Acknowledgments 77
2.8 References 77
Chapter 3 Three-Membered Ring Systems 82
3.1 Introduction 82
3.2 Epoxides 82
3.3 Aziridines 93
3.4 References 103
Chapter 4 Four-Membered Ring Systems 107
4.1 Introduction 107
4.2 Azetidines, azetines, and related systems 107
4.3 Monocyclic 2-azetidinones (ß-lactams) 110
4.4 Fused and spirocyclic ß-lactams 114
4.5 Oxetanes, dioxetanes, oxetanediones and 2-oxetanones ( ß-lactones) 116
4.6 Thietanes, ß-sultams, and related systems 119
4.7 Silicon and phosphorus heterocycles. Miscellaneous 120
4.8 References 121
Chapter 5.1 Five-Membered Ring Systems: Thiophenes and Se/Te Analogues 128
5.1.1 Introduction 128
5.1.2 Thiophene ring synthesis 129
5.1.3 Reactions of thiophenes 132
5.1.4 Non-polymeric thiophene organic materials 137
5.1.5 Thiophene oligomers and polymers 141
5.1.6 Thiophene derivatives in medicinal chemistry 147
5.1.7 Selenophenes and tellurophenes 150
5.1.8 References 152
Chapter 5.2 Five-Membered Ring Systems: Pyrroles and Benzo Analogs 158
5.2.1 Introduction 158
5.2.2 Synthesis of pyrroles 158
5.2.3 Reactions of pyrroles 163
5.2.4 Pyrrole natural products and materials 167
5.2.5 Synthesis of indoles 169
5.2.6 Reactions of indoles 174
5.2.7 Indole natural products 178
5.2.8 Oxindoles and spirooxindoles 180
5.2.9 Carbazoles 181
5.2.10 Azaindoles and carbolines 182
5.2.11 Bioorganic chemistry 183
5.2.12 References 184
Chapter 5.3 Five-Membered Ring Systems: Furans and Benzofurans 192
5.3.1 Introduction 192
5.3.2 Reactions 193
5.3.3 Synthesis 199
5.3.4 References 227
Chapter 5.4 Five Membered Ring Systems: With More than One N Atom 237
5.4.1 Introduction 237
5.4.2 Pyrazoles and ring-fused derivatives 237
5.4.3 Imidazoles and ring-fused derivatives 245
5.4.4 1,2,3-Triazoles and ring-fused derivatives 254
5.4.5 1,2,4-Triazoles and ring-fused derivatives 260
5.4.6 Tetrazoles and ring-fused derivatives 263
5.4.7 References 266
Chapter 5.5 Five-Membered Ring Systems: With N and S (Se) Atoms 274
5.5.1 Introduction 274
5.5.2 Thiazoles 274
5.5.3 Isothiazoles 293
5.5.4 Thiadiazoles and selenodiazoles 300
5.5.5 1,3-Selenazoles, 1,3-selenadolidines and 1,3-tellurazoles 305
5.5.6 References 305
Chapter 5.6 Five-Membered Ring Systems: With O & S (Se, Te) Atoms
5.6.1 1,3-Dioxoles and dioxolanes 309
5.6.2 1,3-Dithioles and dithiolanes 311
5.6.3 1,3-Oxathioles and oxathiolanes 314
5.6.4 1,2-Dioxolanes 315
5.6.5 1,2-Dithioles and dithiolanes 315
5.6.6 1,2-Oxathioles and oxathiolanes 316
5.6.7 Three heteroatoms 316
5.6.8 References 316
Chapter 5.7 Five-Membered Ring Systems with O & N Atoms
5.7.1 Isoxazoles 321
5.7.2 Isoxazolines 324
5.7.3 Isoxazolidines 326
5.7.4 Oxazoles 330
5.7.5 Oxazolines 331
5.7.6 Oxazolidines 335
5.7.7 Oxadiazoles 339
5.7.8 References 339
Chapter 6.1 Six-Membered Ring Systems: Pyridine and Benzo Derivatives 343
6.1.1 Introduction 343
6.1.2 Pyridines 343
6.1.3 Quinolines 356
6.1.4 Isoquinolines 362
6.1.5 Piperidines 365
6.1.6 References 376
Chapter 6.2 Six-Membered Ring Systems: Diazines and Benzo Derivatives 388
6.2.1 Introduction 388
6.2.2 Reviews and general studies 388
6.2.3 Pyridazines and benzo derivatives 389
6.2.4 Pyrimidines and benzo derivatives 393
6.2.5 Pyrazines and benzo derivatives 410
6.2.6 References 416
Chapter 6.3 (2007) Triazines, Tetrazines and Fused Ring Polyaza Systems 428
6.3.1 Triazines 428
6.3.2 Tetrazines 436
6.3.3 Fused [6]+[5] polyaza systems 439
6.3.4 Fused [6]+[6] polyaza systems 443
6.3.5 References 443
Chapter 6.3 (2008) Triazines, Tetrazines and Fused Ring Polyaza Systems 448
6.3.1 Triazines 448
6.3.2 Tetrazines 455
6.3.3 Fused [6]+[5] polyaza systems 457
6.3.4 Fused [6]+[6] polyaza systems 462
6.3.5 References 463
Chapter 6.4 Six-Membered Ring Systems: With O and/or S Atoms 468
6.4.1 Introduction 468
6.4.2 Heterocycles containing one oxygen atom 469
6.4.3 Heterocycles containing one sulfur atom 490
6.4.4 Heterocycles containing two or more oxygen atoms 493
6.4.5 Heterocycles containing two or more sulfur atoms 494
6.4.6 References 495
Chapter 7 Seven-Membered Rings 504
7.1 Introduction 504
7.2 Seven-membered systems containing one heteroatom 504
7.3 Seven-membered systems containing two heteroatoms 514
7.4 Seven-membered systems containing three or more heteroatoms 530
7.5 Seven-membered systems of pharmacological significance 532
7.6 Future directions 537
7.7 References 537
Chapter 8 Eight-Membered and Larger Rings 544
8.1 Introduction 544
8.2 Carbon–oxygen rings 545
8.3 Carbon–nitrogen rings 547
8.4 Carbon–sulfur rings 550
8.5 Carbon–silicon rings 552
8.6 Carbon–arsenic rings 552
8.7 Carbon–nitrogen–oxygen rings 552
8.8 Carbon–nitrogen–sulfur rings 554
8.9 Carbon–sulfur–oxygen rings 555
8.10 Carbon–oxygen–silicon rings 556
8.11 Carbon–nitrogen–phosphorus rings 556
8.12 Carbon–nitrogen–sulfur–oxygen rings 556
8.13 Carbon–nitrogen–boron–oxygen rings 557
8.14 Carbon–nitrogen–phosphorus–sulfur/oxygen rings 557
8.15 Carbon–nitrogen–metal rings 557
8.16 Carbon–nitrogen–oxygen–metal rings 559
8.17 Carbon–nitrogen–sulfur–metal rings 559
8.18 Carbon–phosphorus–oxygen–metal rings 559
8.19 References 559
Index 564

Produkt-Details

• Erscheint lt. Verlag: 3.9.2009
• Sprache: englisch
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Technik
• ISBN-10: 0-08-096516-4 / 0080965164
• ISBN-13: 978-0-08-096516-1 / 9780080965161