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Heterocyclic Chemistry 5th Edition by John A. Joule and Keith Mills
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Heterocyclic Chemistry Contents
- Heterocyclic Nomenclature
- Structures and Spectroscopic Properties of Aromatic Heterocycles
- Substitutions of Aromatic Heterocycles
- Organometallic Heterocyclic Chemistry
- Methods in Heterocyclic Chemistry
- Ring Synthesis of Aromatic Heterocycles
- Typical Reactivity of Pyridines, Quinolines, and Isoquinolines
- Pyridines: Reactions and Synthesis
- Quinolines and Isoquinolines: Reactions and Synthesis
- Typical Reactivity of Pyrylium and Benzopyrylium Ions, Pyrones and Benzopyrones
- Pyryliums, 2- and 4-Pyrones: Reactions and Synthesis
- Benzopyryliums and Benzopyrones: Reactions and Synthesis
- Typical Reactivity of the Diazine: Pyridazine, Pyrimidine, and Pyrazine
- The Diazines: Pyridazine, Pyrimidine, and Pyrazine: Reactions and Synthesis
- Typical Reactivity of Pyrroles, Furans, and Thiophenes
- Pyrroles: Reactions and Synthesis
- Thiophenes: Reactions and Synthesis
- Furans: Reactions and Synthesis
- Typical Reactivity of Indoles, Benzo[b]thiophenes, Benzo[b]furans, Isoindoles, Benzo[c]thiophenes, and Isobenzofurans
- Indoles: Reactions and Synthesis
- Benzo[b]thiophenes and Benzo[b]furans: Reactions and Synthesis
- Isoindoles, Benzo[c]thiophenes, and Isobenzofurans: Reactions and Synthesis
- Typical Reactivity of 1,3- and 1,2-Azoles and Benzo-1,3- and -1,2-Azoles
- 1,3-Azoles: Imidazoles, Thiazoles, and Oxazoles: Reactions and Synthesis
- 1,2-Azoles: Pyrazoles, Isothiazoles, Isoxazoles: Reactions and Synthesis
- Benzanellated Azoles: Reactions and Synthesis
- Purines: Reactions and Synthesis
- Heterocycles Containing a Ring-Junction Nitrogen (Bridgehead Compounds)
- Heterocycles Containing More Than Two Heteroatoms
- Saturated and Partially Unsaturated Heterocyclic Compounds: Reactions and Synthesis
- Special Topics
- Heterocycles in Biochemistry; Heterocyclic Natural Products
- Heterocycles in Medicine
Preface to Heterocyclic Chemistry PDF
Heterocyclic compounds have a wide range of applications but are of particular interest in medicinal chemistry, and this has catalyzed the discovery and development of much heterocyclic chemistry and methods.
The preparation of a fifth edition has allowed us to review thoroughly the material included in the earlier editions, to make amendments in the light of new knowledge, and to include recent work.
Within the restrictions that space dictates, we believe that all of the most significant heterocyclic chemistry of the 20th century and important more recent developments have been covered or referenced.
We have maintained the principal aim of the earlier editions to teach the fundamentals of heterocyclic reactivity and synthesis in a way that is understandable by undergraduate students. However
In recognition of the level at which much heterocyclic chemistry is now normally taught, we include more advanced and current material, which makes the book appropriate both for postgraduate-level courses, and as a reference text for those involved in heterocyclic chemistry in the workplace.
New in this edition is the use of color in the schemes. We have highlighted in red those parts of products (or intermediates) where a change in structure or bonding has taken place.
We hope that this both facilitates comprehension and understanding of the chemical changes that are occurring and, especially for the undergraduate student, quickly focuses attention on just those parts of the molecules where structural change has occurred.
For example, in the first reaction below, only changes at the pyridine nitrogen are involved; in the second example, the introduced bromine resulting from the substitution and its new bond to the heterocycle, are highlighted.
We also show all positive and negative charges in red. In recognition of the enormous importance of organometallic chemistry in heterocyclic synthesis, we have introduced a new chapter dealing exclusively with this aspect.
Chapter 4, ‘ Organometallic Heterocyclic Chemistry ’, has: (i) a general overview of heterocyclic organometallic chemistry, but most examples are to be found in the individual ring chapters, (ii) the use of transition metal-catalyzed reactions that, as a consequence of regularity and consistency that is to a substantial degree independent of the heterocyclic ring
Is best treated as a whole, and therefore most examples are brought together here, with relatively few in the ring chapters. Other innovations in this fifth edition are discussions in Chapter 5 of the modern techniques of (i) solid-phase chemistry, (ii) microwave heating, and (iii) flow reactors in the heterocyclic context.
Reflecting on the large part that heterocyclic chemistry plays in the pharmaceutical industry, there are entirely new chapters that deal with ‘ Heterocycles in Medicine ’ (Chapter 33 ) and ‘ Heterocycles in Biochemistry; Heterocyclic Natural Products ’ (Chapter 32 ).
We devote a new chapter ( 31 ) to some important topics: fluorinated heterocycles, isotopically labeled heterocycles, the use of bioprocesses in heterocyclic transformations, ‘ green chemistry ’, and the somewhat related topic of ionic liquids, and some the applications of heterocyclic compounds in every – day life.
1. The main body of factual material is to be found in chapters entitled ‘ Reactions and synthesis of … ’ a particular heterocyclic system. Didactic material is to be found partly in advanced general discussions of heterocyclic reactivity and synthesis (Chapters 3, 4 and 6 )
And partly in six short summary chapters (such as ‘ Typical Reactivity of Pyridines, Quinolines and Isoquinolines ’; Chapter 7 ), which aim to capture the essence of that typical reactivity in very concise resumés.
These last are therefore suitable as an introduction to the chemistry of that heterocyclic system, but they are insufficient in themselves and should lead the reader to the fuller discussions in the ‘ Reactions and Synthesis of … ’ chapters.
They will also serve the undergraduate student as a revision summary of the typical chemistry of that system.
2. More than 4000 references have been given throughout the text: the references to original work have been chosen as good leading references and are, therefore, not necessarily the first or last mention of that particular topic or method or compound; some others are included as benchmark papers and others for their historical interest.
The extensive list of references is most relevant to post-graduate teaching and to research workers, however, we believe that the inclusion of references does not interfere with the readability of the text for the undergraduate student. Many review references are also included: for these, we give the title of the article; titles are also given for the books to which we refer.
The majority of journals are available only on a subscription (personal or institutional) basis, but most of their web sites give free access to abstracts and a few, such as Arkivoc and Beilstein Journal of Organic Chemistry give free access to full papers.
Free access to the full text of patents, with a search facility, is available via government web sites. Organic Syntheses, the ‘ gold standard ’ for practical organic chemistry, has totally free online access to full procedures.
3. Exercises are given at the ends of most of the substantive chapters. These are divided into straightforward, revision exercises, such as will be relevant to an undergraduate course in heterocyclic chemistry.
More advanced exercises, with solutions given online at www.wiley.com/go/joule, are designed to help the reader to develop understanding and apply the principles of heterocyclic reactivity. References have not been given for the exercises, though all are real examples culled from the literature.
4. We largely avoid the use of ‘ R ’ and ‘ Ar ’ for substituents in the structures in schemes and instead give actual examples. We believe this makes the chemistry easier to assimilate, especially for the undergraduate reader. It also avoids implying a generality that may not be justified.
5. Structures and numbering for heterocyclic systems are given at the beginnings of chapters. Where the commonly used name differs from that used in Chemical Abstracts, the name given in square brackets is the official Chemical Abstracts name, thus: indole [1 H – indole].
We believe that the systematic naming of heterocyclic substances is of importance, not least for use in computerized databases, but it serves little purpose in teaching or for the understanding of the subject and, accordingly, we have devoted only a little space to nomenclature.
The reader is referred to an exposition on this topic 1 and also to the Ring Index of Chemical Abstracts in combination with the Chemical Substances Index, from whence both standardized name and numbering can be obtained for all known systems.
Readers with access to electronic search facilities such as SciFinder and Crossfire can easily find the various names for substances via a search on a drawn structure.
6. There are several general reference works concerned with heterocyclic chemistry, which have been gathered together as a set at the end of this chapter, and to which the reader ’ s attention is drawn.
In order to save space, these vital sources are not repeated in particular chapters, however, all the topics covered in this book are covered in them, and recourse to these sources should form the early basis of any literature search.
7. The literature of heterocyclic chemistry is so vast that the series of nine listings – ‘ The Literature of Heterocyclic Chemistry ’, Parts I – IX 2 – is of considerable value at the start of a literature search.
These listings appear in Advances in Heterocyclic Chemistry, 3 itself a prime source for key reviews on heterocyclic topics; the journal, Heterocycles, also carries many useful reviews specifically in the heterocyclic area.
Progress in Heterocyclic Chemistry4 published by the International Society of Heterocyclic Chemistry 5 also carries reviews and monitors developments in heterocyclic chemistry over a calendar year.
Essential at the beginning of a literature search is a consultation with the appropriate chapter(s) of Comprehensive Heterocyclic Chemistry, the original 6a, and its two updates, 6b,6c, or, for a useful introduction and overview, the handbook 7 to the series.
It is important to realize that particular topics in the three parts of Comprehensive Heterocyclic Chemistry must be read together with the later parts update, but do not repeat, the earlier material.
Finally, the Science of Synthesis series, published over the period 2000 – 2008, contains authoritative discussions of information organized in a hierarchical system. 8 Volumes 9 – 17 discuss aromatic heterocycles.
8. There are three comprehensive compilations of heterocyclic facts: the early series 9 edited by Elderfi eld, discusses pioneering work.
The still – continuing and still – growing series of monographs 10 dealing with particular heterocyclic systems, edited originally by Arnold Weissberger, and latterly by Edward C. Taylor and Peter Wipf, is a vital source of information and reviews for all those working with heterocyclic compounds.
Finally, the heterocyclic volumes of Rodd ’ s Chemistry of Carbon Compounds11 contain a wealth of well – sifted information and data.
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