Progress in heterocyclic chemistry. Vol. 18, A critical review of the 2005 literature preceded by two chapters on current heterocyclic topics için kapak resmi
Başlık:
Progress in heterocyclic chemistry. Vol. 18, A critical review of the 2005 literature preceded by two chapters on current heterocyclic topics
Dil:
English
ISBN:
9780080450254

9780080467573
Edisyon:
1st ed.
Yayın Bilgileri:
Oxford ; Boston : Elsevier, 2007.
Fiziksel Tanımlama:
1 online resource (xi, 457 p.) : ill.
İçerik:
1. The Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone and its derivatives (Heui-Yeon Kim, Cheon-Gyu) -- -- 2. Recent developments in the chemistry of nucleosides (J.-L. Girardet, S. Lang) -- -- 3. Three-membered ring systems -- -- 4. Four-membered ring systems -- -- 5. Five-membered ring systems -- -- 6. Six-membered ring systems -- -- 7. Seven-membered rings -- -- 8. Eight-membered and larger rings.
Özet:
The eighteenth annual volume of Progress in Heterocyclic Chemistry, covers the literature published during 2005 on most of the important heterocyclic ring systems. This volume opens with two specialized reviews. The first, by Heui-Yeon Kim and Cheon-Gyu Cho covers 'The Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone and its derivatives'. The second, by Jean-Luc Girardet and Stanley Lang discusses 'Recent developments in the chemistry of nucleosides'. The remaining chapters examine the 2005 literature on the common heterocycles in order of increasing ring size and the heteroatoms present. References are incorporated into the text using the journal codes adopted by Comprehensive Heterocyclic Chemistry, and are listed in full at the end of each chapter. Included in the index are systematic heterocyclic ring system names. * Includes new contributions from experts in the field * Covers literature published during 2005 on most of the important heterocyclic ring systems * Presents two specialized reviews.

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E-Kitap 1300271-1001 QD400 .P76 2007 v. 18 eb Elsevier E-Kitap Koleksiyonu
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Özet

Özet

The eighteenth annual volume of Progress in Heterocyclic Chemistry, covers the literature published during 2005 on most of the important heterocyclic ring systems. This volume opens with two specialized reviews. The first, by Heui-Yeon Kim and Cheon-Gyu Cho covers 'The Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone and its derivatives'. The second, by Jean-Luc Girardet and Stanley Lang discusses 'Recent developments in the chemistry of nucleosides'. The remaining chapters examine the 2005 literature on the common heterocycles in order of increasing ring size and the heteroatoms present. References are incorporated into the text using the journal codes adopted by Comprehensive Heterocyclic Chemistry, and are listed in full at the end of each chapter. Included in the index are systematic heterocyclic ring system names.


Yazar Notları

Gordon Gribble is the Dartmouth Professor of Chemistry at Dartmouth College, Hanover, USA. His research program covers several areas of organic chemistry, most of which involve synthesis, including novel indole chemistry, triterpenoid synthesis, DNA intercalation, and new synthetic methodology. Prof Gribble also has a deep interest in naturally occurring organohalogen compounds, and in the chemistry of wine and wine making.


İçindekiler

Heui-Yeon Kim and Cheon-Gyu ChoJean-Luc Girardet and Stanley A. LangAlbert Padwa and Shaun MurphreeStephen C. Bergmeier and Damon D. ReedBenito Alcaide and Pedro AlmendrosTomasz Janosik and Jan BergmanErin T. PelkeyXue-Long Hou and Zhen Yang and Kap-Sun Yeung and Henry N. C. WongLarry YetYong-Jin Wu and Bingwei V. YangR. Alan Aitken and Lynn A. PowerStefano Cicchi and Franca M. Cordero and Donatella GiomiHeidi L. Fraser and M. Brawner Floyd and Darrin W. HopperPilar Goya and Cristina Gomez de la OlivaJohn D. Hepworth and B. Mark HeronJohn B. Bremner and Siritron SamosornGeorge R. Newkome
Forewordp. x
Editorial Advisory Board Membersp. xi
Chapter 1 The Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone and its derivativesp. 1
1.1 Overview of the Diels-Alder chemistry of 2-pyronep. 1
1.2 3,5-Dibromo-2-pyronep. 6
1.2.1 [4+2] Cycloadditions of 3.5-dibromo-2-pyronep. 6
1.2.2 Synthesis and cycloadditions of substituted monobromo-2-pyronesp. 14
1.2.3 Intramolecular Diels-Alder cycloadditions of 2-pyronesp. 21
1.3 Conclusionp. 24
1.4 Acknowledgementsp. 24
1.5 Referencesp. 25
Chapter 2 Recent developments in the chemistry of nucleosidesp. 27
2.1 Introductionp. 27
2.2 Sugar chemistryp. 28
2.2.1 Hydrogen and oxygen substitutionsp. 29
2.2.1.1 Modifications at C-1'p. 29
2.2.1.2 Modifications at C-2'p. 29
2.2.1.3 Modifications at C-3'p. 32
2.2.1.4 Modifications at C-4'p. 33
2.2.1.5 Modifications at C-5'p. 34
2.2.2 Ring-oxygen substitutionp. 38
2.2.2.1 Substitution with carbonp. 38
2.2.2.2 Substitution with sulfurp. 40
2.2.2.3 Substitution with nitrogenp. 41
2.2.3 Nucleosides with bicyclic sugarsp. 42
2.2.3.1 Spiro nucleosidesp. 42
2.2.3.2 Bicyclic nucleosidesp. 44
2.3 Combinatorial approachesp. 46
2.4 Conclusionp. 49
2.5 Referencesp. 49
Chapter 3 Three-membered ring systems
Part 1 2004p. 55
3.1.1 Introductionp. 55
3.1.2 Epoxidesp. 55
3.1.2.1 Preparation of epoxidesp. 55
3.1.2.2 Reactions of epoxidesp. 55
3.1.3 Aziridinesp. 69
3.1.3.1 Preparation of aziridinesp. 69
3.1.3.2 Reactions of aziridinesp. 74
3.1.4 Referencesp. 78
Part 2 2005p. 81
3.2.1 Introductionp. 81
3.2.2 Epoxidesp. 81
3.2.2.1 Preparation of epoxidesp. 81
3.2.2.2 Reactions of epoxidesp. 87
3.2.3 Aziridinesp. 95
3.2.3.1 Preparation of aziridinesp. 95
3.2.3.2 Reactions of aziridinesp. 97
3.2.4 Referencesp. 103
Chapter 4 Four-membered ring systemsp. 106
4.1 Introductionp. 106
4.2 Azetidines and azetesp. 106
4.3 Monocyclic 2-azetidinones ([beta]-lactams)p. 109
4.4 Fused polycyclic [beta]-lactamsp. 113
4.5 Oxetanes, dioxetanes, oxetes and 2-oxetanones ([beta]-lactones)p. 115
4.6 Thietanes, [beta]-sultams, and related systemsp. 118
4.7 Silicon and phosphorus heterocycles. miscellaneousp. 118
4.8 Referencesp. 120
Chapter 5 Five-membered ring systems
Part 1 Thiophenes and Se/Te Analoguesp. 126
5.1.1 Introductionp. 126
5.1.2 Thiophene ring synthesisp. 126
5.1.3 Reactions of thiophenesp. 130
5.1.4 Non-polymeric thiophene organic materialsp. 135
5.1.5 Thiophene oligomers and polymersp. 137
5.1.6 Thiophene derivatives in medicinal chemistryp. 141
5.1.7 Selenophenes and tellurophenesp. 143
5.1.8 Referencesp. 144
Part 2 Pyrroles and benzo derivativesp. 150
5.2.1 Introductionp. 150
5.2.2 Synthesis of pyrrolesp. 150
5.2.2.1 Intramolecular approachesp. 151
5.2.2.2 Intermolecular approachesp. 153
5.2.2.3 Transformation of other heterocyclesp. 155
5.2.3 Reactions of pyrrolesp. 156
5.2.3.1 Substitution at nitrogenp. 156
5.2.3.2 Substitution at carbonp. 157
5.2.3.3 Functionalization of the side-chainp. 159
5.2.4 Pyrrole natural products and materialsp. 160
5.2.4.1 Natural productsp. 160
5.2.4.2 Macrocycles and oligopyrrolesp. 161
5.2.4.3 Non-oligomeric materialsp. 162
5.2.5 Synthesis of indolesp. 163
5.2.5.1 Intramolecular approachesp. 163
5.2.5.2 Intermolecular approachesp. 166
5.2.5.3 Transformation of other heterocyclesp. 167
5.2.5.4 Oxindoles, azaindoles, and carbazolesp. 167
5.2.6 Reactions of indolesp. 169
5.2.6.1 Substitution at nitrogenp. 169
5.2.6.2 Substitution at C-2/C-3p. 170
5.2.6.3 Functionalization of the benzene ringp. 175
5.2.6.4 Functionalization of the side-chainp. 176
5.2.7 Indole natural productsp. 177
5.2.7.1 Natural productsp. 177
5.2.8 Referencesp. 178
Part 3 Furans and benzofuransp. 187
5.3.1 Introductionp. 187
5.3.2 Reactionsp. 188
5.3.2.1 Furansp. 188
5.3.2.2 Di- and tetrahydrofuransp. 192
5.3.3 Synthesisp. 194
5.3.3.1 Furansp. 194
5.3.3.2 Di- and tetrahydrofuransp. 199
5.3.3.3 Benzo[b]furans and related compoundsp. 203
5.3.3.4 Benzo[c]furans and related compoundsp. 209
5.3.4 Referencesp. 210
Part 4 With more than One N Atomp. 218
5.4.1 Introductionp. 218
5.4.2 Pyrazoles and ring-fused derivativesp. 218
5.4.3 Imidazoles and ring-fused derivativesp. 225
5.4.4 1,2,3-Triazoles and ring-fused derivativesp. 232
5.4.5 1,2,4-Triazoles and ring-fused derivativesp. 236
5.4.6 Tetrazoles and ring-fused derivativesp. 240
5.4.7 Referencesp. 241
Part 5 With N and S (Se) atomsp. 247
5.5.1 Introductionp. 247
5.5.2 Thiazolesp. 247
5.5.2.1 Synthesis of thiazoles and fused derivativesp. 247
5.5.2.2 Synthesis of thiazolinesp. 252
5.5.2.3 Synthesis of 2-imino-thiazolidine and thiazoline derivativesp. 254
5.5.2.4 Reactions of thiazoles and fused derivativesp. 255
5.5.2.5 Reactions of thiazolinesp. 257
5.5.2.6 Thiazole intermediates in synthesisp. 258
5.5.2.7 Thiazolium-catalyzed and-mediated reactionsp. 261
5.5.2.9 Thiazole-containing drug candidatesp. 264
5.5.2.10 New thiazole-containing natural productsp. 265
5.5.3 Isothiazolesp. 265
5.5.3.1 Synthesis of isothiazoles by ring-formationp. 265
5.5.3.2 Reactions of isothiazolesp. 268
5.5.3.3 Isothiazoles as auxiliaries in organic synthesesp. 268
5.5.3.4 Biologically interesting isothiazolesp. 270
5.5.4 Thiadiazoles and selenadiazolesp. 271
5.5.5 1,3-Selenazoles, 1,3-selenazolidines and 1,3-tellurazolesp. 272
5.5.6 Acknowledgement

p. 273

5.5.7 Referencesp. 273
Part 6 With O and S (Se, Te) atomsp. 276
5.6.1 1,3-Dioxoles and dioxolanesp. 276
5.6.2 1,3-Dithioles and dithiolanesp. 279
5.6.3 1,3-Oxathioles and oxathiolanesp. 282
5.6.4 1,2-Dioxolanesp. 282
5.6.5 1,2-Dithioles and dithiolanesp. 283
5.6.6 1,2-Oxathioles and oxathiolanesp. 283
5.6.7 Three heteroatomsp. 283
5.6.8 Referencesp. 284
Part 7 With O and N atomsp. 289
5.7.1 Isoxazolesp. 288
5.7.2 Isoxazolinesp. 291
5.7.3 Isoxazolidinesp. 294
5.7.4 Oxazolesp. 298
5.7.5 Oxazolinesp. 300
5.7.6 Oxazolidinesp. 304
5.7.7 Oxadiazolesp. 306
5.7.8 Referencesp. 307
Chapter 6 Six-membered ring systems
Part 1 Pyridines and benzo derivativesp. 310
6.1.1 Introductionp. 310
6.1.2 Pyridinesp. 310
6.1.2.1 Preparation of pyridinesp. 310
6.1.2.2 Reactions of pyridinesp. 313
6.1.2.3 Pyridine N-oxides and pyridinium Saltsp. 319
6.1.3 Quinolinesp. 322
6.1.3.1 Preparation of quinolinesp. 322
6.1.3.2 Reactions of quinolinesp. 326
6.1.4 Tsoquinolinesp. 328
6.1.4.1 Preparation of isoquinolinesp. 328
6.1.4.2 Reactions of isoquinolinesp. 331
6.1.5 Piperidinesp. 333
6.1.5.1 Preparations of piperidinesp. 333
6.1.6 Referencesp. 346
Part 2 Diazines and benzo derivativesp. 352
Part 3 Triazines, tetrazines and fused ring polyaza systemsp. 353
6.3.1 Triazinesp. 353
6.3.1.1 1,2,3-Triazinesp. 353
6.3.1.2 1,2,4-Triazinesp. 353
6.3.1.3 1,3,5-Triazinesp. 357
6.3.2 Tetrazinesp. 359
6.3.3 Fused [6]+[5] polyaza systemsp. 361
6.3.3.1 Triazino and tetrazino [6+5] fused systemsp. 361
6.3.3.2 Purines and related structuresp. 363
6.3.4 Fused [6]+[6] polyaza systemsp. 368
6.3.5 Miscellaneous fused polyaza systemsp. 369
6.3.6 Referencesp. 371
Part 4 With O and/or S atomsp. 376
6.4.1 Introductionp. 376
6.4.2 Heterocycles containing one oxygen atomp. 377
6.4.2.1 Pyransp. 377
6.4.2.2 [1]Benzopyrans and dihydro[1]benzopyransp. 380
6.4.2.3 [2]Benzopyrans and dihydro[2]benzopyransp. 382
6.4.2.4 Pyrylium Saltsp. 383
6.4.2.5 Pyranonesp. 384
6.4.2.6 Coumarinsp. 386
6.4.2.7 Chromonesp. 389
6.4.2.8 Xanthones and xanthenesp. 390
6.4.3 Heterocycles containing one sulfur atomp. 391
6.4.3.1 Thiopyrans and analoguesp. 391
6.4.4 Heterocycles containing two or more oxygen atomsp. 393
6.4.4.1 Dioxins and dioxanesp. 393
6.4.4.2 Trioxanesp. 394
6.4.5 Heterocycles containing two or more sulfur atomsp. 395
6.4.5.1 Dithianes and trithianesp. 395
6.4.6 Heterocycles containing both oxygen and sulfur in the same ringp. 396
6.4.6.1 Oxathianesp. 396
6.4.7 Referencesp. 396
Chapter 7 Seven-membered ring systemsp. 402
7.1 Introductionp. 402
7.2 Seven-membered systems containing one heteroatomp. 402
7.2.1 Azepines and derivativesp. 402
7.2.2 Fused azepines and derivativesp. 406
7.2.3 Oxepines and fused derivativesp. 411
7.2.4 Thiepines and fused derivativesp. 412
7.3 Seven-membered systems containing two heteroatomsp. 412
7.3.1 Diazepines and fused derivativesp. 412
7.3.2 Dioxepines, dithiepines and fused derivativesp. 418
7.3.3 Miscellaneous derivatives with two heteroatomsp. 419
7.4 Seven-membered systems containing three or more heteroatomsp. 425
7.4.1 Systems with N, S and/or Op. 425
7.5 Seven-membered systems of pharmacological significancep. 426
7.6 Future directionsp. 427
7.7 Referencesp. 427
Chapter 8 Eight-membered and larger ringsp. 430
8.1 Introductionp. 430
8.2 Carbon-oxygen ringsp. 431
8.3 Carbon-nitrogen ringsp. 433
8.4 Carbon-sulfur ringsp. 436
8.5 Carbon-silicon ringsp. 437
8.6 Carbon-selenium ringsp. 438
8.7 Carbon-oxygen/carbon-nitrogen ringsp. 438
8.8 Carbon-nitrogen-oxygen ringsp. 438
8.9 Carbon-nitrogen-sulfur ringsp. 439
8.10 Carbon-phosphorus-sulfur ringsp. 440
8.11 Carbon-phosphorus-nitrogen ringsp. 440
8.12 Carbon-selenium-nitrogen ringsp. 440
8.13 Carbon-sulfur-oxygen ringsp. 441
8.14 Carbon-nitrogen-sulfur-oxygen ringsp. 442
8.15 Carbon-nitrogen-metal ringsp. 442
8.16 Carbon-phosphorus-metal ringsp. 443
8.17 Carbon-oxygen-nitrogen-metal ringsp. 443
8.18 Carbon-sulfur-nitrogen-metal ringsp. 443
8.19 Carbon-phosphorus-oxygen-metal ringsp. 443
8.20 Referencesp. 444
Indexp. 449