Heterocyclic Chemistry, Fifth Edition; Contents; Preface to the Fifth Edition; P.1 Hazards; P.2 How to Use This Textbook; Acknowledgements; References; Web Site; Biography; Definitions of Abbreviations; 1: Heterocyclic Nomenclature; 2: Structures and Spectroscopic Properties of Aromatic Heterocycles; 2.1 Carbocyclic Aromatic Systems; 2.1.1 Structures of Benzene and Naphthalene; 2.1.2 Aromatic Resonance Energy; 2.2 Structure of Six-Membered Heteroaromatic Systems; 2.2.1 Structure of Pyridine; 2.2.2 Structure of Diazines; 2.2.3 Structure of Pyridinium and Related Cations.
2.2.4 Structures of Pyridones and Pyrones2.3 Structure of Five-Membered Heteroaromatic Systems; 2.3.1 Structure of Pyrrole; 2.3.2 Structures of Thiophene and Furan; 2.3.3 Structures of Azoles; 2.3.4 Structures of Pyrryl and Related Anions; 2.4 Structures of Bicyclic Heteroaromatic Compounds; 2.5 Tautomerism in Heterocyclic Systems; 2.6 Mesoionic Systems; 2.7 Some Spectroscopic Properties of Some Heteroaromatic Systems; 2.7.1 Ultraviolet/Visible (Electronic) Spectroscopy; 2.7.2 Nuclear Magnetic Resonance (NMR) Spectroscopy; References; 3: Substitutions of Aromatic Heterocycles.
3.1 Electrophilic Addition at Nitrogen3.2 Electrophilic Substitution at Carbon; 3.2.1 Aromatic Electrophilic Substitution: Mechanism; 3.2.2 Six-Membered Heterocycles; 3.2.3 Five-Membered Heterocycles; 3.3 Nucleophilic Substitution at Carbon; 3.3.1 Aromatic Nucleophilic Substitution: Mechanism; 3.3.2 Six-Membered Heterocycles; 3.3.3 Vicarious Nucleophilic Substitution (VNS Substitution); 3.4 Radical Substitution at Carbon; 3.4.1 Reactions of Heterocycles with Nucleophilic Radicals; 3.4.2 Reactions with Electrophilic Radicals; 3.5 Deprotonation of N-Hydrogen.
3.6 Oxidation and Reduction of Heterocyclic Rings3.7 ortho-Quinodimethanes in Heterocyclic Compound Synthesis; References; 4: Organometallic Heterocyclic Chemistry; 4.1 Preparation and Reactions of Organometallic Compounds; 4.1.1 Lithium; 4.1.2 Magnesium; 4.1.3 Zinc; 4.1.4 Copper; 4.1.5 Boron; 4.1.6 Silicon and Tin; 4.1.7 Mercury; 4.1.8 Palladium; 4.1.9 Side-Chain Metallation ('Lateral Metallation'); 4.2 Transition Metal-Catalysed Reactions; 4.2.1 Basic Palladium Processes; 4.2.2 Catalysts; 4.2.3 The Electrophilic Partner; The Halides/Leaving Groups; 4.2.4 Cross-Coupling Reactions.
4.2.5 The Nucleophilic (Organometallic) Partner4.2.6 Other Nucleophiles; 4.2.7 The Ring Systems in Cross-Coupling Reactions; 4.2.8 Organometallic Selectivity; 4.2.9 Direct C-H Arylation; 4.2.10 N-Arylation; 4.2.11 Heck Reactions; 4.2.12 Carbonylation Reactions; References; 5: Methods in Heterocyclic Chemistry; 5.1 Solid-Phase Reactions and Related Methods; 5.1.1 Solid-Phase Reactions; 5.1.2 Solid-Supported Reagents and Scavengers; 5.1.3 Solid-Phase Extraction (SPE); 5.1.4 Soluble Polymer-Supported Reactions; 5.1.5 Phase Tags; 5.2 Microwave Heating; 5.3 Flow Reactors; 5.4 Hazards: Explosions.
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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 undergrad.