This expanded second edition provides a concise overview of the main principles and reactions of heterocyclic chemistry for undergraduate students studying chemistry and related courses. Using a successful and student-friendly "e;at a glance"e; approach, this book helps the student grasp the essence of heterocyclic chemistry, ensuring that they can confidently use that knowledge when required. The chapters are thoroughly revised and updated with references to books and reviews; extra examples and student exercises with answers online; and color diagrams that emphasize exactly what is happening in the reaction chemistry depicted.

Professor Emeritus John Joule, Chemistry Department, The University of Manchester, UK
Professor Joule worked for 41 years at the University of Manchester before being appointed Professor Emeritus in 2004. Sabbatical periods were spent at the University of Ibadan, Nigeria, Johns Hopkins Medical School, Department of Pharmacology and Experimental Therapeutics, and the University of Maryland, Baltimore County. He was William Evans Visiting Fellow at Otago University, New Zealand. He has taught many courses on heterocyclic chemistry to industry and academe in the UK and elsewhere. He is currently Associate Editor for Tetrahedron Letters, Scientific Editor for Arkivoc, and Co-Editor of the annual Progress in Heterocyclic Chemistry. He is co-author with Keith Mills of the leading textbook in the field, Heterocyclic Chemistry (Wiley, 5th Edition 2010).

Dr Keith Mills, Independent Consultant, UK
Dr Mills worked in Medicinal Chemistry and Development Chemistry departments of GlaxoSmithKline for a total of 25 years. Since leaving GSK he has been an independent consultant to small pharmaceutical companies. Dr. Mills has worked in several areas of medicine and many areas of organic chemistry, but with particular emphasis on heterocyclic chemistry and the applications of transition metal-catalysed reactions. With John Joule he is co-author of the leading textbook in the field, Heterocyclic Chemistry (Wiley, 5th Edition 2010).

Heterocyclic chemistry is a central part of organic chemistry and biochemistry, dealing with a particular set of chemical structures; organic compounds with a ring structure containing at least one heteroatom (commonly nitrogen, oxygen or sulfur).

Heterocyclic Chemistry at a Glance, Second Edition provides both an introduction and summary of the main principles and reactions of heterocyclic chemistry, for students studying chemistry and related courses at undergraduate level.

This second edition has been much expanded, allowing for a more thorough treatment of key principles and the inclusion of extra examples and illustrations, including heterocycles used in electronics, explosives, polymers, dyestuffs, pigments and that occur in food. All chapters have been revised and updated, including references to books and reviews, and student exercises, with answers on line at http://booksupport.wiley.com. New to this edition is the use of colour in schemes and diagrams highlighting parts of products (or intermediates) where a change in structure or bonding has taken place.

Based on the highly successful and student-friendly "at a glance" approach, the material developed in this book has been chosen to help the student grasp the essence of heterocyclic chemistry, ensuring that they can confidently use that knowledge when required. The structure of the book allows for quick assimilation, understanding and recall of key concepts, facts and definitions, providing an invaluable aid to revision for students preparing for examinations.

Reviews for the first edition:

"This book can be recommended to students looking for a textbook on heterocyclic chemistry. The organization of the material is oriented towards the needs of undergraduate students, but nevertheless the book is comprehensive and will also be of value for more advanced readers."
Heterocycles

Biography v

Abbreviations xii

Introduction to Second Edition xiv

1. Heterocyclic Nomenclature 1

Six-membered aromatic heterocycles 2

Five-membered aromatic heterocycles 2

Non-aromatic heterocycles 3

Small-ring heterocycles 3

2. Structures of Heteroaromatic Compounds 4

Structures of benzene and naphthalene 4

Structures of pyridines and pyridiniums 5

Structures of quinolines and isoquinolines 6

Structures of diazines (illustrated using pyrimidine) 6

Structures of pyrroles, thiophenes and furans 6

Structure of indoles 8

Structures of azoles (illustrated using imidazole) 8

3. Common Reaction Types in Heterocyclic Chemistry 9

Introduction 9

Acidity and basicity 9

Electrophilic substitution of aromatic molecules 10

Nucleophilic substitution of aromatic molecules 13

Radical substitution of heterocycles 14

C-Metallated heterocycles as nucleophiles 15

Generation of C-metallated heterocycles 16

Dimethylformamide dimethyl acetal (DMFDMA) 17

Formation and hydrolysis of imine/enamine 18

Common synthetic equivalents of carbonyl compounds in ring synthesis 19

Cycloaddition reactions 19

4. Palladium in Heterocyclic Chemistry 21

Palladium(0)-catalysed (and related) reactions 21

Addition to alkenes: the Heck reaction 26

Carbonylation reactions 26

Cross-coupling reactions between heteroatom nucleophiles and halides - making carbon-heteroatom bonds 27

Triflates as substrates for palladium-catalysed reactions 27

Mechanisms of palladium(0)-catalysed processes 28

Reactions involving electrophilic palladation 29

Copper-catalysed amination 30

Selectivity 31

5. Pyridines 33

Electrophilic addition to nitrogen 33

Electrophilic substitution at carbon 34

Nucleophilic substitution 35

Nucleophilic addition to pyridinium salts 36

C-metallated pyridines 37

Palladium(0)-catalysed reactions 39

Oxidation and reduction 39

Pericyclic reactions 40

Alkyl and carboxylic acid substituents 40

Oxygen substituents 41

N-Oxides 42

Amine substituents 43

Ring synthesis - disconnections 43

Synthesis of pyridines from 1,5-dicarbonyl compounds 44

Synthesis of pyridines from an aldehyde, two equivalents of a 1,3-dicarbonyl compound and ammonia 45

Synthesis of pyridines from 1,3-dicarbonyl compounds and a C₂N unit 45

Exercises 47

6. Diazines 48

Electrophilic addition to nitrogen 49

Electrophilic substitution at carbon 49

Nucleophilic substitution 50

Radical substitution 52

C-Metallated diazines 52

Palladium(0)-catalysed reactions 53

Pericyclic reactions 54

Oxygen substituents 55

N-Oxides 57

Amine substituents 57

Ring synthesis - disconnections 58

Synthesis of pyridazines from 1,4-dicarbonyl compounds 58

Synthesis of pyrimidines from 1,3-dicarbonyl compounds 58

Synthesis of pyrazines from 1,2-dicarbonyl compounds 59

Synthesis of pyrazines from a-amino-carbonyl compounds 60

Benzodiazines 60

Exercises 61

7. Quinolines and Isoquinolines…