Heterocyclic chemistry:
Saved in:
| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Harlow
Longman
1997
|
| Edition: | 3. ed. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XVII, 414 S. zahlr. Ill. |
| ISBN: | 0582278430 |
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| 245 | 1 | 0 | |a Heterocyclic chemistry |c Thomas L. Gilchrist |
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| 264 | 1 | |a Harlow |b Longman |c 1997 | |
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Record in the Search Index
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| adam_text | Titel: Heterocyclic chemistry
Autor: Gilchrist, Thomas L.
Jahr: 1997
Contents
Preface to the third edition xii
Preface to the second edition xiii
Preface to the first edition xv
Acknowledgements xvii
1 Introduction: uses of heterocyclic compounds
Aromatic heterocycles 8
2.1 The common structural types 8
2.1.1 Six-atom, six-Tr-electron heterocycles 8
2.1.2 Five-atom, six-Tr-electron heterocycles 12
2.1.3 Benzo-fused ring systems 14
2.1.4 Other fused heterocycles 15
2.2 Some criteria of aromaticity in heterocycles 16
2.2.1 Bond lengths 16
2.2.2 Ring current effects and chemical shifts in
¹ NMR spectra 18
2.2.3 Molecular orbitais and delocalization energy 19
2.2.4 Resonance energies 22
2.2.5 Dewar resonance energies and other
calculated resonance energies 24
2.2.6 General conclusions 25
2.3 Aromatic character and other types of unsaturated
heterocycles 26
2.3.1 Monocyclic systems that conform to the
Hiickel rule 26
2.3.2 Other unsaturated heterocycles 28
2.4 Reactivity of heteroaromatic compounds 29
2.5 Tautomerism of heteroaromatic compounds 32
Summary 35
Problems 35
vi Contents
Nonaromatic heterocycles 38
3.1 Introduction 38
3.2 Bond angle strain 39
3.2.1 Angle strain and bonding in small-ring
heterocycles 39
3.2.2 Some consequences of bond angle strain in
small rings 41
3.2.3 Angle strain in larger rings 44
3.3 Torsional energy barriers 44
3.3.1 Single bonds 44
3.3.2 Double bonds and partial double bonds 46
3.4 Influence of bond lengths and van der Waals radii:
conformational preferences of flexible heterocycles 48
3.4.1 Saturated six-membered heterocycles 48
3.4.2 Four- and five-membered heterocycles 50
3.5 Other types of interaction in saturated heterocycles 51
3.5.1 Through-bond orbital interactions: the
anomeric effect 51
3.5.2 Attractive through-space interactions 56
Summary 57
Problems 58
Ring synthesis
4.1 Introduction °
4.2 Cyclization reactions
4.2.1 Reaction types ^2
4.2.2 Displacement at saturated carbon 68
4.2.3 Intramolecular nucleophilic addition to
carbonyl groups
4.2.4 Intramolecular addition of nucleophiles to
other double bonds *
4.2.5 Cyclization on to triple bonds 76
4.2.6 Radical cyclization ™
4.2.7 Carbene and nitrene cyclization 83
4.2.8 Electrocyclic reactions °
4.3 Cycloaddition reactions 89
4.3.1 Reaction types 89
4.3.2 1,3-Dipolar cycloaddition 91
4.3.3 Hetero-Diels-Alder reactions 106
4.3.4 [2 -(- 2] Cycloaddition 115
4.3.5 Cheletropic reactions H8
4.3.6 Ene reactions 120
Summary 121
Problems 121
Contents vii
Six-membered ring compounds with one heteroatom 125
5.1 Introduction 125
5.2 Pyridines 125
5.2.1 Introduction 125
5.2.2 Ring synthesis 127
5.2.3 General features of the chemistry of
pyridines 133
5.2.4 Basicity 136
5.2.5 Alkylation, acylation and complexation on
nitrogen 137
5.2.6 Electrophilic substitution at carbon 138
5.2.7 Nucleophilic substitution 142
5.2.8 Didehydropyridines (pyridynes) 147
5.2.9 Radical substitution 149
5.2.10 Palladium-catalysed coupling reactions and
Heck reactions 149
5.2.11 Reduction of pyridines and pyridinium salts:
dihydropyridines 150
5.2.12 Photochemical isomerization 152
5.2.13 Pyridine iV-oxides, 7V-imides and iV-ylides 153
5.2.14 Hydroxy- and aminopyridines 154
5.2.15 Alkyl- and alkenylpyridines 156
5.2.16 Pyridinecarboxylic acids 158
5.3 Quinolines and isoquinolines 158
5.3.1 Introduction 158
5.3.2 Synthesis of quinolines 159
5.3.3 Synthesis of isoquinolines 162
5.3.4 General features of the chemistry of
quinolines and isoquinolines 164
5.3.5 Electrophilic substitution 165
5.3.6 Nucleophilic substitution 167
5.3.7 Nucleophilic addition 168
5.3.8 Oxidative cleavage 169
5.3.9 JV-Oxides and N-imides 170
5.3.10 Properties of substituents 170
5.3.11 Cyanine dyes 171
5.4 Other fused pyridines 172
5.4.1 Quinolizines 172
5.4.2 Acridines 173
5.4.3 Phenanthridines 175
5.4.4 Indolizines 175
5.5 Ring systems containing oxygen 176
5.5.1 Pyrylium salts 176
5.5.2 2//-Pyran-2-ones 178
5.5.3 4//-Pyran-4-ones 181
5.5.4 Benzo-fused systems 183
viii Contents
Summary
Problems
6 Five-membered ring compounds with one heteroatom
6.1 Introduction
6.2 Pyrroles
6.2.1 Introduction
6.2.2 Ring synthesis
6.2.3 Acidity and metallation reactions
6.2.4 Substitution at nitrogen
6.2.5 Substitution at carbon
6.2.6 Addition and cycloaddition reactions
6.2.7 Properties of substituted pyrroles
6.2.8 Porphyrins and related pyrrolic natural
products
186
187
192
192
193
193
194
197
197
198
204
205
207
6.3 Furans * 208
6.3.1 Introduction 208
6.3.2 Ring synthesis 210
6.3.3 Reactions with electrophiles 212
6.3.4 Radical substitution and nucleophilic
substitution 216
6.3.5 Cycloaddition reactions 216
01Q
6.3.6 Ring-cleavage reactions ¿iy
6.3.7 Some properties of substituted furans 221
6.4 Thiophenes 221
6.4.1 Introduction 221
6.4.2 Ring synthesis 222
6.4.3 Electrophilic substitution 223
6.4.4 Nucleophilic and radical substitution 226
6.4.5 Addition and cycloaddition reactions 228
6.4.6 Reductive desulfurization zz°
6.4.7 Photochemical isomerization 229
6.4.8 Properties of some substituted thiophenes 230
6.5 índoles and related compounds 231
6.5.1 Introduction 23
6.5.2 Ring synthesis 233
6.5.3 Reaction with electrophiles 237
6.5.4 Radical substitution and coupling reactions 241
6.5.5 Oxidation and reduction 24
6.5.6 Properties of some substituted Índoles 243
6.6 Other benzo[è]-fused heterocycles 244
6.6.1 Benzofurans 244
6.6.2 Benzo[è]thiophenes 246
6.6.3 Carbazoles 248
6.7 Benzo[c]-fused heterocycles 249
6.7.1 Introduction
6.7.2 Synthesis
6.7.3 Chemical properties
6.7.4 Phthalocyanines
Summary
Problems
Contents ix
249
249
250
251
252
253
Six-membered ring compounds with two or more
heteroatoms 257
7.1 Introduction 257
7.2 General aspects of the chemistry of diazines, triazines
and tetrazines 257
7.3 Pyrimidines and purines 261
7.3.1 Introduction 261
7.3.2 Synthesis of pyrimidines 264
7.3.3 Synthesis of purines 266
7.3.4 Reactions of pyrimidines 268
7.3.5 Reactions of purines 274
7.3.6 Pyrimidines and purines in nucleic acids 275
7.4 Other diazines, triazines and tetrazines 276
7.4.1 Introduction 276
7.4.2 Methods of ring synthesis 278
7.4.3 Chemical properties 280
7.5 Some fused ring systems 284
7.5.1 Introduction 284
7.5.2 Ring synthesis 285
7.5.3 Chemical properties 286
7.6 Oxazines and thiazines 288
7.6.1 Introduction 288
7.6.2 1,3-Oxazines 289
7.6.3 Phenothiazines 291
Summary 292
Problems 293
Five-membered ring compounds with two or more
heteroatoms 295
8.1 Introduction 295
8.2 Imidazoles 298
8.2.1 Introduction 298
8.2.2 Ring synthesis 299
8.2.3 Reactions 301
8.3 Pyrazoles, triazoles and tetrazoles 304
8.3.1 Introduction 304
8.3.2 Ring synthesis 305
8.3.3 Substitution reactions 308
÷ Contents
8.3.4 Ring cleavage
8.3.5 Azoles as ori/zo-directing groups for
metallation
8.4 Benzodiazoles and benzotriazoles
8.5 Oxazoles and thiazoles and their benzo derivatives
8.5.1 Introduction
8.5.2 Ring synthesis
8.5.3 Chemical properties
8.6 Isoxazoles, isothiazoles and their benzo derivatives
8.6.1 Introduction
8.6.2 Ring synthesis
8.6.3 Chemical properties
8.7 Oxadiazoles, thiadiazoles and related systems
8.7.1 Introduction
8.7.2 Ring synthesis
8.7.3 Chemical properties
8.8 Betaines and mesoionic compounds
8.8.1 JV-Oxides and iV-imides
8.8.2 Mesoionic compounds
Summary
Problems
311
314
315
319
319
320
322
328
328
329
332
335
335
336
336
340
341
341
344
345
Three- and four-membered ring compounds 350
9.1 Introduction 350
9.2 Aziridines 350
9.2.1 Introduction 350
9.2.2 Ring synthesis 351
9.2.3 Functionalization at nitrogen 352
9.2.4 Ring-opening reactions 353
9.2.5 Fragmentation reactions 354
9.3 Oxiranes 354
9.3.1 Introduction 354
9.3.2 Ring synthesis 355
9.3.3 Reactions 357
9.4 Thiiranes 359
9.5 2/7-Azirines 360
9.6 Diaziridines and 3//-diazirines 363
9.7 Oxaziridines 364
9.8 Azetidines and azetidinones 365
9.9 Other four-membered heterocycles 367
9.9.1 Oxetanes 367
9.9.2 Thietanes 368
9.9.3 Some unsaturated four-membered rings 369
Summary 370
Problems 371
Contents xi
10 Seven-membered ring compounds 373
10.1 Introduction 373
10.2 Azepines 374
10.3 Oxepins and thiepins 376
10.4 Diazepines and benzodiazepines 379
Summary 381
Problems 382
11 Nomenclature 384
11.1 Introduction 384
11.2 Trivial names of common ring systems 385
11.3 Systematic (Hantzsch-Widman) nomenclature for
monocyclic compounds 387
11.4 The naming of fused ring systems 389
11.5 Replacement nomenclature 392
Summary 392
Problems 393
Answers and references to selected problems 394
Index 400
|
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| isbn | 0582278430 |
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| spelling | Gilchrist, Thomas L. Verfasser (DE-588)172097606 aut Heterocyclic chemistry Thomas L. Gilchrist 3. ed. Harlow Longman 1997 XVII, 414 S. zahlr. Ill. txt rdacontent n rdamedia nc rdacarrier Compostos heterocíclicos larpcal Química larpcal Heterocyclic chemistry Heterocyclische Verbindungen (DE-588)4159726-6 gnd rswk-swf (DE-588)4123623-3 Lehrbuch gnd-content Heterocyclische Verbindungen (DE-588)4159726-6 s DE-604 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008429366&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Gilchrist, Thomas L. Heterocyclic chemistry Compostos heterocíclicos larpcal Química larpcal Heterocyclic chemistry Heterocyclische Verbindungen (DE-588)4159726-6 gnd |
| subject_GND | (DE-588)4159726-6 (DE-588)4123623-3 |
| title | Heterocyclic chemistry |
| title_auth | Heterocyclic chemistry |
| title_exact_search | Heterocyclic chemistry |
| title_full | Heterocyclic chemistry Thomas L. Gilchrist |
| title_fullStr | Heterocyclic chemistry Thomas L. Gilchrist |
| title_full_unstemmed | Heterocyclic chemistry Thomas L. Gilchrist |
| title_short | Heterocyclic chemistry |
| title_sort | heterocyclic chemistry |
| topic | Compostos heterocíclicos larpcal Química larpcal Heterocyclic chemistry Heterocyclische Verbindungen (DE-588)4159726-6 gnd |
| topic_facet | Compostos heterocíclicos Química Heterocyclic chemistry Heterocyclische Verbindungen Lehrbuch |
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