Elsevier S & T

Progress in Heterocyclic Chemistry

Gribble, Gordon W.; Joule, J.

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Table of contents
  • Table of Contentsv
  • Forewordx
  • Editorial Advisory Board Membersxi
  • Chapter 1: Recent progress in the chemistry of 2,1-benzothiazines1
  • 1.1 Introduction1
  • 1.2 The synthesis of 2,1-benzothiazines and related compounds1
  • 1.2.1 Synthesis of 3,4-dihydro-2,1-benzothiazine 2,2-dioxide derivatives1
  • 1.2.2 Synthesis of dibenzo[c,e][1,2]thiazine 5,5-dioxide derivatives5
  • 1.2.3 Synthesis of 1H-2,1-benzothiazine 2,2-dioxide (sulfostyril) derivatives7
  • 1.2.4 Synthesis of azathiabenzenes and azathiaphenanthrenes9
  • 1.2.5 Synthesis of 1,2-thiazine S-oxide by cycloaddition of N-sulfinylaniline10
  • 1.2.6 Synthesis of Harmata-type benzothiazines12
  • 1.2.6.1 Lewis acid-mediated synthesis of 2,1-benzothiazenes12
  • 1.2.6.2 Synthesis of enantiomerically pure 2,1-benzothiazines14
  • 1.2.7 Heterocyclic ring-fused thiazines and ring-fused 2,1-benzothiazine derivatives20
  • 1.3 Chemistry of 2,1-benzothiazines25
  • 1.3.1 Reactions of 2,1-benzothiazine 2,2-dioxide25
  • 1.3.2 Reactions of azathiabenzenes and azathiaphenanthrenes26
  • 1.3.3 Functionalization of Harmata-type benzothiazines via a sulfoximine-stablized vinyl carbanion31
  • 1.3.4 Indole Synthesis31
  • 1.3.5 Aniline Synthesis32
  • 1.3.6 Chiral ligands in asymmetric allylic alkylation34
  • 1.3.7 New chiral benzothiazine ligand for catalysis and molecular recognition36
  • 1.3.8 Application of 2,1-benzothiazines in natural products syntheses36
  • 1.4 Acknowledgements40
  • 1.5 References40
  • Chapter 2: Porphyrins in Diels-Alder and 1,3-dipolar cycloaddition reactions44
  • 2.1 Overview of the cycloaddition reactions of porphyrins44
  • 2.2 Porphyrins in cycloaddition reactions45
  • 2.2.1 Porphyrins as dienophiles in Diels-Alder reactions45
  • 2.2.2 Porphyrins as 1,3-dipoles in 1,3-dipolar cycloadditions49
  • 2.2.3 Porphyrins as dipolarophiles in 1,3-dipolar cycloadditions58
  • 2.3 Conclusions67
  • 2.4 Acknowledgements67
  • 2.5 References67
  • Chapter 3: Three-membered ring systems70
  • 3.1 Introduction70
  • 3.2 Epoxides70
  • 3.2.1 Preparation of epoxides70
  • 3.2.2 Reactions of epoxides74
  • 3.3 Aziridines80
  • 3.3.1 Preparation of aziridines80
  • 3.3.2 Reactions of aziridines85
  • 3.4 References90
  • Chapter 4: Four-membered ring systems92
  • 4.1 Introduction92
  • 4.2 Azetidines, azetines, 3-azetidinones, and diazetines92
  • 4.3 Monocyclic 2-azetidinones (β-lactams)95
  • 4.4 Fused and spirocyclic β-lactams98
  • 4.5 Oxetanes, dioxetanes, oxetenes and 2-oxetanones (β-lactones)100
  • 4.6 Thietanes, β-sultams, and related systems103
  • 4.7 Silicon and phosphorus heterocycles. miscellaneous104
  • 4.8 References106
  • Chapter 5: Five-membered ring systems112
  • Part 1. Thiophenes and Se/Te analogs112
  • 5.1.1 Introduction112
  • 5.1.2 Thiophene ring synthesis112
  • 5.1.3 Reactions of thiophenes116
  • 5.1.4 Non-polymeric thiophene organic materials121
  • 5.1.5 Thiophene oligomers and polymers123
  • 5.1.6 Thiophene derivatives in medicinal chemistry125
  • 5.1.7 Selenophenes and tellurophenes127
  • 5.1.8 References128
  • Part 2. Pyrroles and benzo analogs135
  • 5.2.1 Introduction135
  • 5.2.2 Synthesis of pyrroles135
  • 5.2.2.1 Intramolecular approaches135
  • 5.2.2.2 Intermolecular approaches138
  • 5.2.2.3 Transformations of other heterocycles142
  • 5.2.3 Reactions of pyrroles143
  • 5.2.3.1 Substitution at nitrogen143
  • 5.2.3.2 Substitution at carbon143
  • 5.2.3.3 Functionalization of the side-chain148
  • 5.2.4 Pyrrole natural products and materials148
  • 5.2.4.1 Natural products and biologically active small molecules148
  • 5.2.4.2 Macrocycles and oligopyrroles149
  • 5.2.4.3 Non-oligomeric materials149
  • 5.2.5 Synthesis of indoles150
  • 5.2.5.1 Intramolecular approaches151
  • 5.2.5.2 Intermolecular approaches154
  • 5.2.6 Reactions of indoles155
  • 5.2.6.1 Substitution at C–3/C–2155
  • 5.2.6.2 Substitution at nitrogen158
  • 5.2.6.3 Functionalization of the benzene ring158
  • 5.2.6.4 Functionalization of the side-chain159
  • 5.2.7 Carbazoles and azaindoles159
  • 5.2.7.1 Carbazole ring synthesis and annulation159
  • 5.2.7.2 Azaindole ring synthesis160
  • 5.2.8 Indole natural products160
  • 5.2.8.1 Natural products isolation and characterization160
  • 5.2.8.2 Indole alkaloid total synthesis161
  • 5.2.8.3 β-Carboline and tetrahydro-β-carboline total synthesis163
  • 5.2.8.4 Oxindole total synthesis163
  • 5.2.9 Biochemical and medicinal chemistry164
  • 5.2.9.1 Indole alkaloid biosynthesis164
  • 5.2.9.2 Medicinal applications of indole alkaloids165
  • 5.2.10 References165
  • Part 3. Furans and benzofurans176
  • 5.3.1 Introduction176
  • 5.3.2 Reactions177
  • 5.3.2.1 Furans177
  • 5.3.2.2 Di- and tetrahydrofurans181
  • 5.3.3 Synthesis184
  • 5.3.3.1 Furans184
  • 5.3.3.2 Di- and tetrahydrofurans188
  • 5.3.3.3 Benzo[b]furans and related compounds193
  • 5.3.3.4 Benzo[c]furans and related compounds198
  • 5.3.4 References200
  • Part 4. With more than One N Atom208
  • 5.4.1 Introduction208
  • 5.4.2 Pyrazoles and ring-fused derivatives208
  • 5.4.3 Imidazoles and ring-fused derivatives219
  • 5.4.4 1,2,3-Triazoles and ring-fused derivatives226
  • 5.4.5 1,2,4-Triazoles and ring-fused derivatives231
  • 5.4.6 Tetrazoles and ring-fused derivatives233
  • 5.4.7 References235
  • Part 5. With N and S (Se) atoms242
  • 5.5.1 Introduction242
  • 5.5.2 Thiazoles242
  • 5.5.2.1 Synthesis of thiazoles242
  • 5.5.2.2 Synthesis of fused thiazoles245
  • 5.5.2.3 Synthesis of thiazolines247
  • 5.5.2.4 Reactions of thiazoles and fused derivatives249
  • 5.5.2.5 Thiazole intermediates in synthesis254
  • 5.5.2.6 Thiazolium-catalyzed and -mediated reactions258
  • 5.5.2.7 Thiazole-containing natural products261
  • 5.5.2.8 Thiazole-containing drug candidates262
  • 5.5.3 Isothiazoles263
  • 5.5.3.1 Synthesis of isothiazoles263
  • 5.5.3.2 Reactions of isothiazoles266
  • 5.5.3.3 Isothiazoles as auxiliaries in organic syntheses268
  • 5.5.3.4 Pharmaceutically interesting isothiazoles270
  • 5.5.4 Thiadiazoles271
  • 5.5.5 1,3-Selenazoles, 1,3-selenazolidines and 1,2,3-selenadiazoles272
  • 5.5.6 Acknowledgement273
  • 5.5.7 References274
  • Part 6. With O and S (Se, Te) atoms277
  • 5.6.1 1,3-Dioxoles and dioxolanes277
  • 5.6.2 1,3-Dithioles and dithiolanes280
  • 5.6.3 1,3-Oxathioles and oxathiolanes282
  • 5.6.4 1,2-Dioxolanes283
  • 5.6.5 1,2-Dithioles and dithiolanes283
  • 5.6.6 1,2-Oxathioles and oxathiolanes283
  • 5.6.7 Three heteroatoms283
  • 5.6.8 References284
  • Part 7. With O and N atoms288
  • 5.7.1 Isoxazoles288
  • 5.7.2 Isoxazolines291
  • 5.7.3 Isoxazolidines294
  • 5.7.4 Oxazoles298
  • 5.7.5 Oxazolines302
  • 5.7.6 Oxazolidines306
  • 5.7.7 Oxadiazoles309
  • 5.7.8 References310
  • Chapter 6: Six-membered ring systems314
  • Part 1. Pyridine and benzo derivatives314
  • 6.1.1 Introduction314
  • 6.1.2 Pyridines314
  • 6.1.2.1 Preparation of pyridines314
  • 6.1.2.2 Reactions of pyridines318
  • 6.1.2.3 Pyridine N-oxides and pyridinium Salts322
  • 6.1.3 Quinolines325
  • 6.1.3.1 Preparation of quinolines325
  • 6.1.3.2 Reactions of quinolines328
  • 6.1.4 Isoquinolines330
  • 6.1.4.1 Preparation of isoquinolines330
  • 6.1.4.2 Reactions of isoquinolines332
  • 6.1.5 Piperidines333
  • 6.1.5.1 Preparations of piperidines334
  • 6.1.6 References343
  • Part 2 (2005) Diazines and benzo derivatives (2005)353
  • 6.2.1 Introduction353
  • 6.2.2 Reviews and general studies353
  • 6.2.3 Pyridazines and benzo derivatives354
  • 6.2.3.1 Syntheses355
  • 6.2.3.2. Reactions356
  • 6.2.3.3 Applications356
  • 6.2.4 Pyrimidines and benzo derivatives357
  • 6.2.4.1 Syntheses360
  • 6.2.4.2 Reactions365
  • 6.2.4.3 Applications367
  • 6.2.5 Pyrazines and benzo derivatives370
  • 6.2.5.1 Syntheses371
  • 6.2.5.2 Reactions372
  • 6.2.5.3 Applications373
  • 6.2.6 References374
  • Part 2 (2006) Diazines and benzo derivatives (2006)383
  • 6.2.1 Introduction383
  • 6.2.2 General studies383
  • 6.2.3 Pyridazines and benzo derivatives385
  • 6.2.3.1 Synthesis385
  • 6.2.3.2 Reactions388
  • 6.2.4 Pyrimidines and benzo derivatives389
  • 6.2.4.1 Synthesis390
  • 6.2.4.2 Reactions400
  • 6.2.4.3 Applications405
  • 6.2.5 Pyrazines and benzo derivatives406
  • 6.2.5.1 Synthesis406
  • 6.2.5.2 Reactions407
  • 6.2.5.3 Applications and structural studies409
  • 6.2.6 References410
  • Part 3. Triazines, tetrazines and fused ring polyaza systems414
  • 6.3.1 Triazines414
  • 6.3.1.1 1,2,3-Triazines414
  • 6.3.1.2 1,2,4-Triazines415
  • 6.3.1.3 1,3,5-Triazines416
  • 6.3.2 Tetrazines420
  • 6.3.3 Fused [6]+[5] polyaza systems422
  • 6.3.3.1 Triazino and tetrazino [6+5] fused systems422
  • 6.3.3.2 Purines and related structures423
  • 6.3.4 Fused [6]+[6] polyaza systems427
  • 6.3.5 Miscellaneous428
  • 6.3.6 References429
  • Part 4. With O and/or S atoms436
  • Chapter 7: Seven-membered rings437
  • 7.1 Introduction437
  • 7.2 Seven-membered systems containing one heteroatom437
  • 7.2.1 Azepines and derivatives437
  • 7.2.2 Fused azepines and derivatives442
  • 7.2.3 Oxepines and fused derivatives445
  • 7.2.4 Thiepines and fused derivatives448
  • 7.3 Seven-membered systems containing two heteroatoms449
  • 7.3.1 Diazepines and fused derivatives449
  • 7.3.2 Dioxepines, dithiepines and fused derivatives452
  • 7.3.3 Miscellaneous derivatives with two heteroatoms453
  • 7.4 Seven-membered systems containing three of more heteroatoms457
  • 7.4.1 Systems with N, S and/or O457
  • 7.5 Seven-membered systems of pharmacological significance459
  • 7.6 Future directions461
  • 7.7 References461
  • Chapter 8: Eight-membered and larger rings465
  • 8.1 Introduction465
  • 8.2 Carbon-oxygen rings466
  • 8.3 Carbon-nitrogen rings468
  • 8.4 Carbon-sulfur rings470
  • 8.5 Carbon-oxygen/carbon-nitrogen rings471
  • 8.6 Carbon-nitrogen-oxygen rings471
  • 8.7 Carbon-nitrogen-sulfur rings474
  • 8.8 Carbon-phosphorus-oxygen rings475
  • 8.9 Carbon-phosphorus-sulfur rings475
  • 8.10 Carbon-sulfur-oxygen rings476
  • 8.11 Carbon-nitrogen-sulfur-oxygen rings476
  • 8.12 Carbon-silicon/selenium/tellurium rings477
  • 8.13 Carbon-metal rings477
  • 8.14 Carbon-nitrogen-metal rings478
  • 8.15 Carbon-oxygen-nitrogen-metal rings478
  • 8.16 Carbon-silicon/germanium-nitrogen-metal rings479
  • 8.17 Carbon-phosphorus-oxygen-metal rings479
  • 8.18 Referencees479
  • Index484
Book details
  • Vendor Elsevier S & T
  • SKU 9780080454078
  • ISBN-13 9780080553085
  • Author Gribble, Gordon W.; Joule, J.
  • Category Science
  • Subject Organic

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Description eBook delivery & access Reviews
This is the 19th annual volume of Progress in Heterocyclic Chemistry, which covers the literature published during 2006. As with previous volumes in the series, Volume 19 will enable the reader to keep abreast of developments in heterocyclic chemistry in an effortless way.

A critical review of the heterocyclic literature published during 2006

Presents specialized reviews

Chapters all written by leading researchers in their field