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 ofHeterocyclic 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:

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.

Keith Mills spent 25 years in the Medicinal Chemistry and Development Chemistry departments at GlaxoSmithKline, Stevenage, UK, and is now an independent consultant.

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