This book has so closely matched the requirements of itsreadership over the years that it has become the first choice forchemists worldwide. Heterocyclic chemistry comprises at least half of all organicchemistry research worldwide.

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

Heterocyclic chemistry is a central part of organic chemistry and biochemistry. The term refers to a particular set of chemical structure characteristics, with many drugs and specialty chemicals, and most agrochemicals, containing these characteristics. Heterocyclic Chemistry by Joule & Mills has established itself as the premier textbook of heterocyclic chemistry, used by high level undergraduates, postgraduates and industrial researchers all over the world. Heterocyclic Chemistry covers the fundamentals of heterocyclic reactivity and synthesis in a way that is understandable to second- and third-year undergraduate chemistry students. It also includes more advanced material, making the book appropriate for postgraduate taught courses and to researchers, either at postgraduate degree level or those working with heterocyclic compounds in industry. Essential teaching material is collected in specific introductory chapters, explaining the principles of heterocyclic reactivity in the simplest terms, suitable either as introductions or as summaries for examination preparation. These chapters are augmented by detailed, systematic discussions of the chemical reactivity of particular heterocyclic systems. References to both primary literature and reviews are given throughout the text, and whilst these are essential for postgraduate teaching and to research workers, they do not interfere with the readability of the text for undergraduate students.

“Overall, this book is recommended as a text for undergraduate 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, and thoroughly indexed. Accordingly, it serves as both an instructional heterocyclic chemistry textbook and a portal to the primary synthetic chemistry literature." (Journal of Medicinal Chemistry, 2011) "My favourite chapter is the organometallic chemistry that presents an up-to-date treatment of the topic and helps confirms a colleague's observation that ‘With today's techniques one can be convinced that a modern organic chemist can make any small molecule he or she desires.' I particularly like the treatment of the concatenation of five-membered ring systems, an increasingly important 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 a class of its own and can be thoroughly recommended as supplementary reading for undergraduate courses and as a first port of call for researchers seeking a quick entry to the extensive heterocyclic literature." (Applied Organometallic Chemistry, 2010) "My recommendation is, even if you already have the 4th edition, to buy the latest version. At only £39.95 for the paperback version this is outstanding value for money." (Organic Process Research & Development Journal, 2010)