Table of Contents

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 andDevelopment Chemistry departments at GlaxoSmithKline, Stevenage,UK, and is now an independent consultant.

Reviews

Overall, this book is recommended as a text forundergraduate and more advanced students on this pervasive,important, and underappreciated topic in chemistry. (Journal of Chemical Education, 1 October 2012) "This excellent book is well written, heavily referenced, andthoroughly indexed. Accordingly, it serves as both an instructionalheterocyclic chemistry textbook and a portal to the primarysynthetic chemistry literature." (Journal of Medicinal Chemistry,2011) "My favourite chapter is the organometallic chemistry thatpresents an up-to-date treatment of the topic and helps confirms acolleague's observation that With today's techniques one canbe convinced that a modern organic chemist can make any smallmolecule he or she desires.' I particularly like the treatment ofthe concatenation of five-membered ring systems, an increasinglyimportant area in medicinal chemistry. This chapter proves a real coup de grace'." (Reviews, December 2010) "In summary, Heterocyclic Chemistry by Joule and Mills is in aclass of its own and can be thoroughly recommended as supplementaryreading for undergraduate courses and as a first port of call forresearchers seeking a quick entry to the extensive heterocyclicliterature." (Applied Organometallic Chemistry, 2010) "My recommendation is, even if you already have the 4th edition,to buy the latest version. At only GBP39.95 for the paperbackversion this is outstanding value for money." (Organic ProcessResearch & Development Journal, 2010)