Progress in Heterocyclic Chemistry

by Gribble, Gordon W.; Joule, John A.

• ISBN13: 9780080968056
• ISBN10: 0080968058
• Format: Hardcover
• Copyright: 2011-11-07
• Publisher: Elsevier Science Ltd

Summary

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 23 constitute a systematic survey of the important original material reported in the literature of heterocyclic chemistry in 2010. As with previous volumes in the series, Volume 23 apprises academic/industrial chemists and advanced students of developments in heterocyclic chemistry in a convenient format. * Covers the heterocyclic literature published in 2010 * Includes specialized reviews * Features contributions from leading researchers in their fields

Table of Contents

Recent Advances in the Synthesis of Aspidosperma-Jype Alkaloids	p. 1
Introduction	p. 1
Aspidospermine and Aspidospermidine	p. 2
Aspidofractinine	p. 4
Tabersonine	p. 5
Subincanadines	p. 7
Meloscine	p. 9
Miscellaneous Approaches to the General Aspidosperma Core	p. 10
Vindoline, Vinblastine, and Vincristine	p. 11
Aspidophytine and Haplophytine	p. 14
Conophylline and Conophyliidine	p. 21
References	p. 23
Synthesis of Heterocycles by Palladium-Catalyzed Intramolecular Heteroarylation	p. 27
Introduction and Scope of the Review	p. 27
Annulation of Five-Membered Aza-Rings	p. 28
Annulation of Six-Membered Aza-Rings	p. 45
Annulation of Medium Size Aza-Rings	p. 56
Macrocycles	p. 60
Tandem Sequences, Cascades, and Miscellaneous Cyclizations	p. 63
Conclusions	p. 71
References
Three-Membered Ring Systems	p. 75
Introduction	p. 75
Epoxides	p. 75
Aziridines	p. 85
References	p. 95
Four-Membered Ring Systems	p. 101
Introduction	p. 101
Azetidines, Azetines, and Related Systems	p. 101
Monocyclic 2-azetidinones (ß-lactams)	p. 105
Fused and Spirocyclic ß-lactams	p. 109
Oxetanes, Dioxetanes, Dioxetanones, and 2-oxetanones (ß-lactones)	p. 112
Thietanes and Related Systems	p. 116
Silicon and Phosphorus Heterocycles: Miscellaneous	p. 117
References	p. 119
Five-Membered Ring Systems: Thiophenes and Se/Te Derivatives	p. 127
Introduction	p. 127
Reviews, Accounts, and Books on Thiophene, Selenophene, and Tellurophene Chemistry	p. 127
Synthesis of Thiophenes	p. 128
Elaboration of Thiophenes and Benzothiophenes	p. 135
Synthesis of Thiophenes For Use in Material Science	p. 141
Thiophene Derivatives in Medicinal Chemistry	p. 144
Selenophenes and Tellurophenes	p. 147
References	p. 151
Five-Membered Ring Systems: Pyrroles and Benzo Analogs	p. 155
Introduction	p. 155
Synthesis of Pyrroles	p. 155
Reactions of Pyrroles	p. 162
Synthesis of Indoles	p. 170
Reactions of Indoles	p. 176
Oxindoles and Spirooxindoles	p. 185
Carbazoles	p. 186
Carboline Analogs and Azaindoles	p. 186
References	p. 188
Five-Membered Ring Systems: Furans and Benzofurans	p. 195
Introduction	p. 195
Reactions	p. 196
Synthesis	p. 203
References	p. 223
Five-Membered Ring Systems: With More than One N Atom	p. 231
Introduction	p. 231
Pyrazoles and Ring-fused Derivatives	p. 231
Imidazoles and Ring-fused Derivatives	p. 237
1,2,3-Triazoles and Ring-fused Derivatives	p. 244
1,2,4-Triazoles and Ring-fused Derivatives	p. 251
Tetrazoles and Ring-fused Derivatives	p. 254
References	p. 257
Five-Membered Ring Systems: With N and S (Se) Atoms	p. 267
Introduction	p. 267
Thiazoles	p. 267
Isothiazoles	p. 280
Thiadiazoles and Selenodiazoles	p. 285
Selenazoles	p. 289
References	p. 290
Five-Membered Ring Systems: With O and S (Se, Te) Atoms	p. 293
1,3-Dioxoles and 1,3-Dioxolanes	p. 293
1,3-Dithioles and 1,3-Dithiolanes	p. 295
1,3-Oxathioles and 1,3-Oxathiolanes	p. 298
1,2-Dioxolanes	p. 299
1,2-Dithioles and 1,2-Dithiolanes	p. 299
1,2-Oxathioles and 1,2-Oxathiolanes	p. 300
Three Heteroatoms	p. 300
References	p. 300
Five-Membered Ring Systems with O and N Atoms	p. 303
Isoxazoles	p. 303
Isoxazolines	p. 307
Isoxazolidines	p. 310
Oxazoles	p. 313
Oxazolines	p. 316
Oxazolidines	p. 320
Oxadiazoles	p. 324
References	p. 324
Six-Membered Ring Systems: Pyridines and Benzo Derivatives	p. 329
Introduction	p. 329
Pyridines	p. 330
Quinolines	p. 349
Isoquinolines	p. 358
References	p. 364
Six-Membered Ring Systems: Diazines and Benzo Derivatives	p. 371
Introduction	p. 371
Pyridazines and Benzo Derivatives	p. 372
Pyrimidines and Benzo Derivatives	p. 376
Pyrazines and Benzo Derivatives	p. 386
References	p. 395
Triazines, Tetrazines, and Fused Ring Polyaza Systems	p. 403
Introduction	p. 403
Triazines	p. 403
Tetrazines	p. 412
Fused [6] + [5] Polyaza Systems	p. 419
Fused [6] + [6] Polyaza Systems	p. 422
References	p. 423
Six-Membered Ring Systems: With 0 and/or S Atoms	p. 427
Introduction	p. 427
Heterocydes Containing One Oxygen Atom	p. 428
Heterocydes Containing One Sulfur Atom	p. 452
Heterocydes Containing Two or More Oxygen Atoms	p. 454
Heterocydes Containing Two or More Sulfur Atoms	p. 456
Heterocydes Containing Both Oxygen and Sulfur in the Same Ring	p. 457
References	p. 458
Seven-Membered Rings	p. 465
Introduction	p. 465
Seven-Membered Systems Containing One Heteroatom	p. 465
Seven-Membered Systems Containing Two Heteroatoms	p. 475
Seven-membered Systems Containing Three or More Heteroatoms	p. 494
Future Directions	p. 499
References	p. 499
Eight-Membered and Larger Rings	p. 505
Introduction	p. 505
Carbon-Oxygen Rings	p. 506
Carbon-Nitrogen Rings	p. 510
Carbon-Sulfur Rings	p. 514
Carbon-Silicon Rings	p. 515
Carbon-Oxygen/Carbon-Nitrogen-Oxygen Rings	p. 515
Carbon-Nitrogen-Oxygen Rings	p. 516
Carbon-Nitrogen-Phosphorus Rings	p. 517
Carbon-Nitrogen-Sulfur Rings	p. 517
Carbon-Sulfur-Oxygen Rings	p. 518
Carbon-Sulfur-Phosphorus/Arsenic/Antimony/Bismuth Rings	p. 519
Carbon-Nitrogen-Sulfur-Oxygen Rings	p. 519
Carbon-Selenium-Iron Rings	p. 520
References	p. 520
Index	p. 525
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