Heterocyclic Chemistry

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 undergraduate chemistry students. The inclusion of more advanced and current material also makes the book a valuable reference text for postgraduate taught courses, postgraduate researchers, and chemists at all levels working with heterocyclic compounds in industry. Fully updated and expanded to reflect important 21st century advances, the fifth edition of this classic text includes the following innovations: Extensive use of colour to highlight changes in structure and bonding during reactions Entirely new chapters on organometallic heterocyclic chemistry, heterocyclic natural products, especially in biochemical processes, and heterocycles in medicine New sections focusing on heterocyclic fluorine compounds, isotopically labeled heterocycles, and solid-phase chemistry, microwave heating and flow reactors in the heterocyclic context Essential teaching material in the early chapters is followed by short chapters throughout the text which capture the essence of heterocyclic reactivity in concise resum s suitable as introductions or summaries, for example for examination preparation. Detailed, systematic discussions cover the reactivity and synthesis of all the important heterocyclic systems. Original references and references to reviews are given throughout the text, vital for postgraduate teaching and for research scientists. Problems, divided into straightforward revision exercises, and more challenging questions (with solutions available online), help the reader to understand and apply the principles of heterocyclic reactivity and synthesis.

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. In particular, the vast majority oforganic work done in the pharmaceutical and agrochemical industriesis heterocyclic chemistry.The fifth edition of Heterocyclic Chemistry maintains theprincipal objective of earlier editions - to teach thefundamentals of heterocyclic reactivity and synthesis in a way thatis understandable to second- and third-year undergraduate chemistrystudents. The inclusion of more advanced and current material alsomakes the book a valuable reference text for postgraduate taughtcourses, postgraduate researchers, and chemists at all levelsworking with heterocyclic compounds in industry.Fully updated and expanded to reflect important 21stcentury advances, the fifth edition of this classic text includesthe following innovations:* Extensive use of colour to highlight changes in structure andbonding during reactions* Entirely new chapters on organometallic heterocyclic chemistryheterocyclic natural products, especially in biochemical processesand heterocycles in medicine* New sections focusing on heterocyclic fluorine compoundsisotopically labeled heterocycles, and solid-phase chemistrymicrowave heating and flow reactors in the heterocycliccontextEssential teaching material in the early chapters is followed byshort chapters throughout the text which capture the essence ofheterocyclic reactivity in concise resumés suitable asintroductions or summaries, for example for examinationpreparation. Detailed, systematic discussions cover the reactivityand synthesis of all the important heterocyclic systems. Originalreferences and references to reviews are given throughout the textvital for postgraduate teaching and for research scientists.Problems, divided into straightforward revision exercises, and morechallenging questions (with solutions available online), help thereader to understand and apply the principles of heterocyclicreactivity and synthesis.

Preface to the Fifth Edition xixP.1 Hazards xxiP.2 How to Use This Textbook xxiAcknowledgements xxiiReferences xxiiWeb Site xxiiBiography 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