Heterocyclic Chemistry

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 GlaxoSmithKline, Stevenage, UK, and is now an independent consultant.

• Preface to the Fifth Edition xixP.1 Hazards xxiP.2 How to Use This Textbook xxiAcknowledgements xxiiReferences xxiiWeb Site xxii     Biography xxiiiDefinitions of Abbreviations xxv1 Heterocyclic Nomenclature 12 Structures and Spectroscopic Properties of Aromatic Heterocycles 53 Substitutions of Aromatic Heterocycles 194 Organometallic Heterocyclic Chemistry 375 Methods in Heterocyclic Chemistry 976 Ring Synthesis of Aromatic Heterocycles 1077 Typical Reactivity of Pyridines, Quinolines and Isoquinolines 1158 Pyridines: Reactions and Synthesis 1259 Quinolines and Isoquinolines: Reactions and Synthesis 17710 Typical Reactivity of Pyrylium and Benzopyrylium Ions, Pyrones and Benzopyrones 20511 Pyryliums, 2- and 4-Pyrones: Reactions and Synthesis 20912 Benzopyryliums and Benzopyrones: Reactions and Synthesis 22913 Typical Reactivity of the Diazine: Pyridazine, Pyrimidine and Pyrazine 24914 The Diazines: Pyridazine, Pyrimidine, and Pyrazine: Reactions and Synthesis 25315 Typical Reactivity of Pyrroles, Furans and Thiophenes 28916 Pyrroles: Reactions and Synthesis 29517 Thiophenes: Reactions and Synthesis 32518 Furans: Reactions and Synthesis 34719 Typical Reactivity of Indoles, Benzo[b]thiophenes, Benzo[b]furans, Isoindoles, Benzo[c]thiophenes and Isobenzofurans 36920 Indoles: Reactions and Synthesis 37321 Benzo[b]thiophenes and Benzo[b]furans: Reactions and Synthesis 43322 Isoindoles, Benzo[c]thiophenes and Isobenzofurans: Reactions and Synthesis 44723 Typical Reactivity of 1,3- and 1,2-Azoles and Benzo-1,3- and -1,2-Azoles 45524 1,3-Azoles: Imidazoles, Thiazoles and Oxazoles: Reactions and Synthesis 46125 1,2-Azoles: Pyrazoles, Isothiazoles, Isoxazoles: Reactions and Synthesis 48526 Benzanellated Azoles: Reactions and Synthesis 50327 Purines: Reactions and Synthesis 51528 Heterocycles Containing a Ring-Junction Nitrogen (Bridgehead Compounds) 53929 Heterocycles Containing More Than Two Heteroatoms 55730 Saturated and Partially Unsaturated Heterocyclic Compounds: Reactions and Synthesis 58731 Special Topics 60932 Heterocycles in Biochemistry; Heterocyclic Natural Products 62933 Heterocycles in Medicine 645Index 665

“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)