Gribble / Joule Progress in Heterocyclic Chemistry

1. Auflage 2009
ISBN: 978-0-08-096516-1
Verlag: Elsevier Science & Techn.
Format: EPUB
Kopierschutz: 6 - ePub Watermark

E-Book, Englisch, 572 Seiten

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

Autoren/Hrsg.

Gribble, Gordon

Joule, J.

Inhaltsverzeichnis

1;Front Cover;1
2;Progress in Heterocyclic Chemistry;4
3;Copyright Page;5
4;Contents;6
5;Foreword;12
6;Chapter 1 Biocatalytic Approaches to Chiral Heterocycles;14
6.1;1.1 Introduction;14
6.2;1.2 Enzyme classes discussed;14
6.3;1.3 Three-membered ring systems;16
6.4;1.4. Four-membered ring systems;20
6.5;1.5 Five-membered ring systems;24
6.6;1.6 Six-membered ring systems;31
6.7;1.7 Seven-membered and larger ring systems;38
6.8;1.8 Conclusion;41
6.9;1.9 References;41
7;Chapter 2 Ring-Expanded (‘fat’) Purines and their Nucleoside/ Nucleotide Analogues as Broad-Spectrum Therapeutics;48
7.1;2.1 Introduction;48
7.2;2.2 Significance of ‘fat’ purines and their nucleoside/nucleotide analogues;48
7.3;2.3 Chemistry;52
7.4;2.4 Biochemical and biophysical chemistry;61
7.5;2.5 Biological activity;71
7.6;2.6 Conclusion;76
7.7;2.7 Acknowledgments;77
7.8;2.8 References;77
8;Chapter 3 Three-Membered Ring Systems;82
8.1;3.1 Introduction;82
8.2;3.2 Epoxides;82
8.3;3.3 Aziridines;93
8.4;3.4 References;103
9;Chapter 4 Four-Membered Ring Systems;107
9.1;4.1 Introduction;107
9.2;4.2 Azetidines, azetines, and related systems;107
9.3;4.3 Monocyclic 2-azetidinones (ß-lactams);110
9.4;4.4 Fused and spirocyclic ß-lactams;114
9.5;4.5 Oxetanes, dioxetanes, oxetanediones and 2-oxetanones ( ß-lactones);116
9.6;4.6 Thietanes, ß-sultams, and related systems;119
9.7;4.7 Silicon and phosphorus heterocycles. Miscellaneous;120
9.8;4.8 References;121
10;Chapter 5.1 Five-Membered Ring Systems: Thiophenes and Se/Te Analogues;128
10.1;5.1.1 Introduction;128
10.2;5.1.2 Thiophene ring synthesis;129
10.3;5.1.3 Reactions of thiophenes;132
10.4;5.1.4 Non-polymeric thiophene organic materials;137
10.5;5.1.5 Thiophene oligomers and polymers;141
10.6;5.1.6 Thiophene derivatives in medicinal chemistry;147
10.7;5.1.7 Selenophenes and tellurophenes;150
10.8;5.1.8 References;152
11;Chapter 5.2 Five-Membered Ring Systems: Pyrroles and Benzo Analogs;158
11.1;5.2.1 Introduction;158
11.2;5.2.2 Synthesis of pyrroles;158
11.3;5.2.3 Reactions of pyrroles;163
11.4;5.2.4 Pyrrole natural products and materials;167
11.5;5.2.5 Synthesis of indoles;169
11.6;5.2.6 Reactions of indoles;174
11.7;5.2.7 Indole natural products;178
11.8;5.2.8 Oxindoles and spirooxindoles;180
11.9;5.2.9 Carbazoles;181
11.10;5.2.10 Azaindoles and carbolines;182
11.11;5.2.11 Bioorganic chemistry;183
11.12;5.2.12 References;184
12;Chapter 5.3 Five-Membered Ring Systems: Furans and Benzofurans;192
12.1;5.3.1 Introduction;192
12.2;5.3.2 Reactions;193
12.3;5.3.3 Synthesis;199
12.4;5.3.4 References;227
13;Chapter 5.4 Five Membered Ring Systems: With More than One N Atom;237
13.1;5.4.1 Introduction;237
13.2;5.4.2 Pyrazoles and ring-fused derivatives;237
13.3;5.4.3 Imidazoles and ring-fused derivatives;245
13.4;5.4.4 1,2,3-Triazoles and ring-fused derivatives;254
13.5;5.4.5 1,2,4-Triazoles and ring-fused derivatives;260
13.6;5.4.6 Tetrazoles and ring-fused derivatives;263
13.7;5.4.7 References;266
14;Chapter 5.5 Five-Membered Ring Systems: With N and S (Se) Atoms;274
14.1;5.5.1 Introduction;274
14.2;5.5.2 Thiazoles;274
14.3;5.5.3 Isothiazoles;293
14.4;5.5.4 Thiadiazoles and selenodiazoles;300
14.5;5.5.5 1,3-Selenazoles, 1,3-selenadolidines and 1,3-tellurazoles;305
14.6;5.5.6 References;305
15;Chapter 5.6 Five-Membered Ring Systems: With O & S (Se, Te) Atoms;309
15.1;5.6.1 1,3-Dioxoles and dioxolanes;309
15.2;5.6.2 1,3-Dithioles and dithiolanes;311
15.3;5.6.3 1,3-Oxathioles and oxathiolanes;314
15.4;5.6.4 1,2-Dioxolanes;315
15.5;5.6.5 1,2-Dithioles and dithiolanes;315
15.6;5.6.6 1,2-Oxathioles and oxathiolanes;316
15.7;5.6.7 Three heteroatoms;316
15.8;5.6.8 References;316
16;Chapter 5.7 Five-Membered Ring Systems with O & N Atoms;321
16.1;5.7.1 Isoxazoles;321
16.2;5.7.2 Isoxazolines;324
16.3;5.7.3 Isoxazolidines;326
16.4;5.7.4 Oxazoles;330
16.5;5.7.5 Oxazolines;331
16.6;5.7.6 Oxazolidines;335
16.7;5.7.7 Oxadiazoles;339
16.8;5.7.8 References;339
17;Chapter 6.1 Six-Membered Ring Systems: Pyridine and Benzo Derivatives;343
17.1;6.1.1 Introduction;343
17.2;6.1.2 Pyridines;343
17.3;6.1.3 Quinolines;356
17.4;6.1.4 Isoquinolines;362
17.5;6.1.5 Piperidines;365
17.6;6.1.6 References;376
18;Chapter 6.2 Six-Membered Ring Systems: Diazines and Benzo Derivatives;388
18.1;6.2.1 Introduction;388
18.2;6.2.2 Reviews and general studies;388
18.3;6.2.3 Pyridazines and benzo derivatives;389
18.4;6.2.4 Pyrimidines and benzo derivatives;393
18.5;6.2.5 Pyrazines and benzo derivatives;410
18.6;6.2.6 References;416
19;Chapter 6.3 (2007) Triazines, Tetrazines and Fused Ring Polyaza Systems;428
19.1;6.3.1 Triazines;428
19.2;6.3.2 Tetrazines;436
19.3;6.3.3 Fused [6]+[5] polyaza systems;439
19.4;6.3.4 Fused [6]+[6] polyaza systems;443
19.5;6.3.5 References;443
20;Chapter 6.3 (2008) Triazines, Tetrazines and Fused Ring Polyaza Systems;448
20.1;6.3.1 Triazines;448
20.2;6.3.2 Tetrazines;455
20.3;6.3.3 Fused [6]+[5] polyaza systems;457
20.4;6.3.4 Fused [6]+[6] polyaza systems;462
20.5;6.3.5 References;463
21;Chapter 6.4 Six-Membered Ring Systems: With O and/or S Atoms;468
21.1;6.4.1 Introduction;468
21.2;6.4.2 Heterocycles containing one oxygen atom;469
21.3;6.4.3 Heterocycles containing one sulfur atom;490
21.4;6.4.4 Heterocycles containing two or more oxygen atoms;493
21.5;6.4.5 Heterocycles containing two or more sulfur atoms;494
21.6;6.4.6 References;495
22;Chapter 7 Seven-Membered Rings;504
22.1;7.1 Introduction;504
22.2;7.2 Seven-membered systems containing one heteroatom;504
22.3;7.3 Seven-membered systems containing two heteroatoms;514
22.4;7.4 Seven-membered systems containing three or more heteroatoms;530
22.5;7.5 Seven-membered systems of pharmacological significance;532
22.6;7.6 Future directions;537
22.7;7.7 References;537
23;Chapter 8 Eight-Membered and Larger Rings;544
23.1;8.1 Introduction;544
23.2;8.2 Carbon–oxygen rings;545
23.3;8.3 Carbon–nitrogen rings;547
23.4;8.4 Carbon–sulfur rings;550
23.5;8.5 Carbon–silicon rings;552
23.6;8.6 Carbon–arsenic rings;552
23.7;8.7 Carbon–nitrogen–oxygen rings;552
23.8;8.8 Carbon–nitrogen–sulfur rings;554
23.9;8.9 Carbon–sulfur–oxygen rings;555
23.10;8.10 Carbon–oxygen–silicon rings;556
23.11;8.11 Carbon–nitrogen–phosphorus rings;556
23.12;8.12 Carbon–nitrogen–sulfur–oxygen rings;556
23.13;8.13 Carbon–nitrogen–boron–oxygen rings;557
23.14;8.14 Carbon–nitrogen–phosphorus–sulfur/oxygen rings;557
23.15;8.15 Carbon–nitrogen–metal rings;557
23.16;8.16 Carbon–nitrogen–oxygen–metal rings;559
23.17;8.17 Carbon–nitrogen–sulfur–metal rings;559
23.18;8.18 Carbon–phosphorus–oxygen–metal rings;559
23.19;8.19 References;559
24;Index;564