This book has so closely matched the requirements of its
readership over the years that it has become the first choice for
chemists worldwide.
Heterocyclic chemistry comprises at least half of all organic
chemistry research worldwide. In particular, the vast majority of
organic work done in the pharmaceutical and agrochemical industries
is heterocyclic chemistry.
The fifth edition of Heterocyclic Chemistry maintains the
principal objective of earlier editions – to teach the
fundamentals of heterocyclic reactivity and synthesis in a way that
is understandable to second- and third-year undergraduate chemistry
students. The inclusion of more advanced and current material also
makes the book a valuable reference text for postgraduate taught
courses, postgraduate researchers, and chemists at all levels
working with heterocyclic compounds in industry.
Fully updated and expanded to reflect important 21st
century advances, the fifth edition of this classic text includes
the following innovations:
* Extensive use of colour to highlight changes in structure and
bonding during reactions
* Entirely new chapters on organometallic heterocyclic chemistry,
heterocyclic natural products, especially in biochemical processes,
and heterocycles in medicine
* New sections focusing on heterocyclic fluorine compounds,
isotopically labeled heterocycles, and solid-phase chemistry,
microwave heating and flow reactors in the heterocyclic
context
Essential teaching material in the early chapters is followed by
short chapters throughout the text which capture the essence of
heterocyclic reactivity in concise resumés suitable as
introductions or summaries, for example for examination
preparation. Detailed, systematic discussions cover the reactivity
and synthesis of all the important heterocyclic systems. Original
references and references to reviews are given throughout the text,
vital for postgraduate teaching and for research scientists.
Problems, divided into straightforward revision exercises, and more
challenging questions (with solutions available online), help the
reader to understand and apply the principles of heterocyclic
reactivity and synthesis.
Зміст
Preface to the Fifth Edition xix
P.1 Hazards xxi
P.2 How to Use This Textbook xxi
Acknowledgements xxii
References xxii
Web Site xxii
Biography xxiii
Definitions of Abbreviations xxv
1 Heterocyclic Nomenclature 1
2 Structures and Spectroscopic Properties of Aromatic Heterocycles 5
3 Substitutions of Aromatic Heterocycles 19
4 Organometallic Heterocyclic Chemistry 37
5 Methods in Heterocyclic Chemistry 97
6 Ring Synthesis of Aromatic Heterocycles 107
7 Typical Reactivity of Pyridines, Quinolines and Isoquinolines 115
8 Pyridines: Reactions and Synthesis 125
9 Quinolines and Isoquinolines: Reactions and Synthesis 177
10 Typical Reactivity of Pyrylium and Benzopyrylium Ions, Pyrones and Benzopyrones 205
11 Pyryliums, 2- and 4-Pyrones: Reactions and Synthesis 209
12 Benzopyryliums and Benzopyrones: Reactions and Synthesis 229
13 Typical Reactivity of the Diazine: Pyridazine, Pyrimidine and Pyrazine 249
14 The Diazines: Pyridazine, Pyrimidine, and Pyrazine: Reactions and Synthesis 253
15 Typical Reactivity of Pyrroles, Furans and Thiophenes 289
16 Pyrroles: Reactions and Synthesis 295
17 Thiophenes: Reactions and Synthesis 325
18 Furans: Reactions and Synthesis 347
19 Typical Reactivity of Indoles, Benzo[b]thiophenes, Benzo[b]furans, Isoindoles, Benzo[c]thiophenes and Isobenzofurans 369
20 Indoles: Reactions and Synthesis 373
21 Benzo[b]thiophenes and Benzo[b]furans: Reactions and Synthesis 433
22 Isoindoles, Benzo[c]thiophenes and Isobenzofurans: Reactions and Synthesis 447
23 Typical Reactivity of 1, 3- and 1, 2-Azoles and Benzo-1, 3- and -1, 2-Azoles 455
24 1, 3-Azoles: Imidazoles, Thiazoles and Oxazoles: Reactions and Synthesis 461
25 1, 2-Azoles: Pyrazoles, Isothiazoles, Isoxazoles: Reactions and Synthesis 485
26 Benzanellated Azoles: Reactions and Synthesis 503
27 Purines: Reactions and Synthesis 515
28 Heterocycles Containing a Ring-Junction Nitrogen (Bridgehead Compounds) 539
29 Heterocycles Containing More Than Two Heteroatoms 557
30 Saturated and Partially Unsaturated Heterocyclic Compounds: Reactions and Synthesis 587
31 Special Topics 609
32 Heterocycles in Biochemistry; Heterocyclic Natural Products 629
33 Heterocycles in Medicine 645
Index 665
Про автора
John Joule is Emeritus Professor in the School of Chemistry,
The University of Manchester, UK
Keith Mills spent 25 years in the Medicinal Chemistry and
Development Chemistry departments at Glaxo Smith Kline, Stevenage,
UK, and is now an independent consultant.
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