John A. Joule & Keith Mills 
Heterocyclic Chemistry 

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.

Table of Content

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

About the author

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.