Advances in Heterocyclic Chemistry Volume 100

Advances in Heterocyclic Chemistry
 
Author:
Alan R. Katritzky
Publisher: Academic Press
ISBN No: 978-0-12-380936-0
Release at: 2010
Pages: 271
Edition:
Volume 100
File Size: 3 MB
File Type: pdf
Language: English



Description of Advances in Heterocyclic Chemistry Volume 100


Volume 100 of Advances in Heterocyclic Chemistry commences with a chapter by C. A. Ramsden (University of Keele, UK) on 1,2-benzoquinones as a precursor of a wide variety of heterocycles. Catherine L. Lucas and C. J. Moody (University of Nottingham, UK) provide a summary of naturally occurring 1,4-thiazines, a compound class that has been extensively investigated recently; much information on the synthesis and properties of important derivatives is included.

S. A. Raw (AstraZeneca, UK) and R. J. K. Taylor (University of York, UK) describe novel developments in the preparation and applications of 1,2,4-triazines, especially inverse electron demand Diels–Alder reactions.

Heteroaryl radicals, with particular emphasis on pyridyl, indolyl, and thienyl radicals, in which the unpaired electron occupies an sp2 orbital orthogonal to the p-system are covered by D. Mirizzi and K. Jones (Institute of Cancer Research, London, UK) and S. T. Hilton (School of Pharmacy, University of London, UK). B. Stanovnik and U. GrosĖ‡elj (University of Ljubljana, Slovenia) review applications of acetone-1,3-dicarboxylates in heterocyclic synthesis with emphasis on pyrazole- and pyrimidine-derived ring systems. A. P. Sadimenko (University of Fort Hare, South Africa) reports on some of the remarkable advances in organometallic chemistry of heterocycles, which have occurred in the last decade.

Content of Advances in Heterocyclic Chemistry Volume 100



CHAPTER 1
1. Introduction 1
2. Addition Reactions 3
2.1 Intermolecular cycloadditions 3
2.2 Intramolecular additions 17
3. Addition–Elimination Reactions 20
3.1 Intermolecular addition–elimination 20
3.2 Intramolecular addition–elimination 35
4. Ring-Opening Reactions 36
4.1 Ring-expansion reactions 36
4.2 Ring-contraction reactions 36
4.3 New six-membered rings 37
References 38

CHAPTER 2
1. Introduction 54
2. Di- and Tetrahydro-1,4-thiazines and their S-oxides 56
2.1 Deoxychondrine 56
2.2 Chondrine 56
2.3 Cycloalliin 57
2.4 Tetrahydro-1,4-thiazine-3,5-dicarboxylic acid 57
2.5 3,4-Dihydro-6-(4-hydroxyphenyl)-1,4-thiazine-1,1-
dioxide 57
3. Benzo-1,4-thiazines 58
3.1 Antibiotic BMY 40662 58
3.2 The xanthiazones 58
3.3 The aplidinones 59
3.4 The thiazinotrienomycins and antibiotics TMC-135A
and TMC-135B 60
3.5 The trichochromes 62
4. Tricyclic Thiazines 62
4.1 The conicaquinones and ascidiathiazones 62
4.2 Ansathiazin 64
4.3 FR901537 64
4.4 The euthyroideones 65

CHAPTER 3
1. Introduction 76
2. Synthesis of 1,2,4-triazines 76
2.1 Condensations of 1,2-dicarbonyls and equivalents 76
2.2 Oxidative approaches 78
2.3 1,2,4-Triazine-N-oxides and their derivitisation 78
2.4 Miscellaneous approaches 80
3. Functionalisation of the 1,2,4-triazine Heteroaromatic Ring 81
3.1 Dimerisation 82
3.2 Substitution chemistry of 1,2,4-triazines 82
3.3 Substituent activation 84
4. Inverse Electron Demand aza-Diels–Alder Reactions of
1,2,4-Triazines 85
4.1 With enamines 85
4.2 With alkenes 88
4.3 With enol ethers 89
4.4 With alkynes 90
5. Cascade Reactions of 1,2,4-triazines 92
5.1 From 1,2,4-Triazines to polycyclic ring systems 92
5.2 4,5-Dihydroazocines 94
6. Use of 1,2,4-Triazines in Total Synthesis 95
6.1 Semipervirine 95
6.2 Epibatidine 95
6.3 Louisianins A–D 96
7. Summary 96
References 97

CHAPTER 4
1. Introduction 101
2. Pyridyl radicals 102
3. Indolyl radicals 115
4. Thienyl radicals 125
5. Quinolyl and isoquinolyl radicals 129
6. Other heteroaromatic radicals 131
7. Summary 138
List of abbreviations 139
References 139

CHAPTER 5
1. Introduction 146
2. Transformations of Dialkyl Acetone-1,3-Dicarboxylates
and their (Dimethylamino)methylidene Derivatives 146
2.1 Synthesis of 1-substituted 4-ethoxycarbonyl-5-
(ethoxycarbonylmethyl)pyrazoles 147
2.2 Synthesis of pyrazolo[4,3-c]pyridine derivatives 149
2.3 Synthesis of pyrazolo[4,3-d][1,2]diazepine derivatives 153
2.4 Synthesis of fused pyrazol-3-yl-pyrimidine derivatives
and fused pyrazol-3-yl-pyranones 156
2.5 Synthesis of pyrazolo[1,5-c]pyrimidin-5-one
derivatives synthesis of 7-amino-3-ethoxycarbonyl-
pyrazolo[1,5-c]pyrimidin-5(1H)-one (08ACSi1019) 157
2.6 Synthesis of pyridin-4(1H)ones (06H899) 158
2.7 Synthesis of 4-hydroxypyridin-2(1H)-one and pyrano
[3,2-c]pyridinone derivatives 161
2.8 Synthesis of thiazolo[5,4-c]pyridine derivatives 162
2.9 Synthesis of 4-oxo-1,4-dihydropyridazine-3,5-
dicarboxylates 162
2.10 Synthesis of heteroaryl substituted pyrimidine
derivatives 165

CHAPTER 6
1. Introduction 175
2. Remarkable organometallic compounds 176
2.1 Five-membered monoheterocycles 176
2.2 Azoles 178
2.3 Pyridines 183
2.4 Six-membered heterocycles with two or more
heteroatoms 187
2.5 Five- and six-membered rings with transition metal
heteroatoms 188
3. Conclusion 190
List of Abbreviations 191
References 191

CHAPTER 7
1. Introduction 196
2. Physical properties and theoretical chemistry 197
2.1 Electronic spectra 197
2.2 Infrared spectra 199
2.3 Mass spectra 199
2.4 Nuclear magnetic resonance spectra 199
2.5 Electron spin resonance spectra and cyclic voltammetry 200
2.6 Theoretical chemistry 201
2.7 X-ray crystallography 204
3. Synthesis of the [1,2,3]triazolo[1,5-a]pyridine system 210
4. Synthesis of novel aryltriazolopyridines 211
4.1 Synthesis of aryltriazolopyridines by Suzuki cross-coupling reactions 211
4.2 Deprotonative magnesation and cadmation of [1,2,3] triazolo[1,5-a]pyridines 214
4.3 Direct arylation on triazolopyridines 216
5. Chiral ligands from [1,2,3]triazolo[1,5-a]pyridines 219
6. A new route to 2,2u-bipyridines from [1,2,3]triazolo[1,5-a] pyridines 226
7. Pyridylcarbene formation from triazolopyridines 228
8. Ring-chain isomerization on [1,2,3]triazolo[1,5-a]pyridines 232
9. Novel pyridylcarbonylpyridines 234
9.1 Synthesis from triazolopyridines 235
9.2 Applications 240
10. Triazolopyridines as building blocks in supramolecular chemistry 244
11. Pharmacological studies 246
11.1 Synthesis and evaluation of
7-arylhydroxymethyltriazolopyridines as potential cardiovascular agents 247
11.2 Biological evaluation of [1,2,3]triazolo[1,5-a]pyridines as new neural nitric oxide synthase inhibitors 247
References 248

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