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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