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Heterocyclic Chemistry, 5th Edition

ISBN: 978-1-4051-3300-5
718 pages
June 2010, Wiley-Blackwell
Heterocyclic Chemistry, 5th Edition (1405133007) cover image
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 resumés 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.

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Preface

Definitions of abbreviations

1. Heterocyclic nomenclature

2. Structures and spectroscopic properties of aromatic heterocycles

3. Substitutions of aromatic heterocycles

4. Organometallic heterocyclic chemistry

5. Methods in heterocyclic chemistry

6. Ring synthesis of aromatic heterocycles

7. Typical reactivity of pyridines, quinolines and isoquinolines

8. Pyridines: reactions and synthesis

9. Quinolines and isoquinolines: reactions and synthesis

10. Typical reactivity of pyrylium and benzopyrylium ions, pyrones and benzopyrones

11. Pyryliums, 2- and 4-pyrones: reactions and synthesis

12. Benzopyryliums, benzopyrones: reactions and synthesis

13. Typical reactivity of the diazines: pyridazine, pyrimidine and pyrazine

14. The diazines: pyridazine, pyrimidine, and pyrazine: reactions and synthesis

15. Typical reactivity of pyrroles, thiophenes, and furans

16. Pyrroles: reactions and synthesis

17. Thiophenes: reactions and synthesis

18. Furans: reactions and synthesis

19. Typical reactivity of indoles, benzo[b]thiophenes, benzo[b]furans, isoindoles, benzo[c]thiophenes and isobenzofurans

20. Indoles: reactions and synthesis

21. Benzo[b]thiophenes and benzo[b]furans: reactions and synthesis

22. Isoindoles, benzo[c]thiophenes and isobenzofurans: reactions and synthesis

23. Typical reactivity of 1,3- and 1,2-azoles and benzo-1,3- and -1,2-azoles

24. 1,3-Azoles: imidazoles, thiazoles, and oxazoles: reactions and synthesis

25. 1,2-Azoles: pyrazoles, isothiazoles, isoxazoles: reactions and synthesis

26. Benzanellated azoles: reactions and synthesis

27. Purines: reactions and synthesis

28. Heterocycles containing a ring-junction nitrogen (bridgehead compounds)

29. Heterocycles containing more than two heteroatoms

30. Saturated and partially unsaturated heterocyclic compounds: reactions and synthesis

31. Special topics

32. Heterocycles in biochemistry; heterocyclic natural products

33. Heterocycles in medicine

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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.

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  • The authors have thoroughly reviewed the material included in the earlier Editions, to make amendments in the light of new knowledge, and to include many important 21st Century advances
  • Entirely, new sections include ‘Organometallic heterocyclic chemistry’, ‘Heterocycles in medicine’, reflecting the large part that heterocyclic chemistry plays in the pharmaceutical industry, and ‘Heterocycles in biochemistry; heterocyclic natural products’.
  • Also included are new sections dealing explicitly with a number of topics important in the heterocyclic context: (i) heterocyclic fluorine compounds, (ii) isotopically labeled heterocycles, and (iii) the modern techniques of solid-phase chemistry, microwave heating and flow reactors.
  • Two colour diagrams indicate where a change in structure or bonding has taken place, facilitating comprehension and understanding of the chemical changes that are occurring.
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  • The use of colour in the schemes clearly highlights those parts of products (or intermediates) where a change in structure or bonding has taken place, facilitating comprehension and understanding of the chemical changes that are occurring.

  • Essential teaching material in the early chapters aims to capture the essence of heterocyclic reactivity in concise resumes suitable either as introductions, or as revisions/summaries for examination preparation.

  • Problems, divided into straightforward revision exercises and more challenging questions (with solutions as an Appendix), help the reader to understand and apply the principles of heterocyclic reactivity and synthesis.

  • All of the most significant heterocyclic chemistry of the 20th Century and many important 21st Century advances are covered.

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“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)

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June 01, 2010
Heterocyclic Chemistry, 5th Edition

The Fifth Edition of the recognized gold-standard for students of heterocyclic chemistry is now published by Wiley-Blackwell.  Heterocyclic Chemistry, 5th Edition, now thoroughly revised and updated to reflect 21st Century advances in the field, further establishes itself as the authoritative compendium of choice for the practicing chemist.

Heterocyclic chemistry is a central part of organic chemistry and biochemistry, comprising over half of all organic chemistry research worldwide, and the vast majority of that done in the pharmaceutical and agrochemical industries. An understanding of the chemistry of heterocycles is essential in the study and application of organic chemistry, as well as being a central part of the increasingly popular medicinal and pharmaceutical chemistry degree courses.

Heterocyclic Chemistry, 5th Edition has so closely matched the requirements of its readership over the years that it has become the first choice for high level chemistry undergraduates, postgraduates and industrial researchers all over the world.  This new edition includes entirely new chapters on organometallic heterocyclic chemistry and heterocycles in biochemistry and medicine,   reflecting the large part that heterocyclic chemistry plays in the pharmaceutical industry. All of the most significant heterocyclic chemistry of the 20th Century and many important 21st Century advances are covered in this easy to read, compact and concise text.

The principle aim of Heterocyclic Chemistry has always been to teach the fundamentals of heterocyclic reactivity and synthesis in a way that is understandable by undergraduate students. This has been maintained whilst also including more advanced and current material for professional chemists involved in heterocyclic chemistry in the workplace. Problems, divided into straightforward revision exercises and more challenging questions, help the reader to understand and apply the principles of heterocyclic reactivity and synthesis. New in this Fifth Edition is the use of color in the schemes, emphasizing changes in structure or bonding.

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