Heterocyclic Chemistry, 3rd Edition: 3rd Edition (Paperback) book cover

Heterocyclic Chemistry, 3rd Edition

3rd Edition

By John Joule, Keith Mills, George Smith

CRC Press

534 pages

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pub: 1995-10-20
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Description

Covering the fundamentals of heterocyclic reactivity and synthesis, this book teaches the subject in a way that is understandable to graduate students. Recognizing the level at which heterocyclic chemistry is often taught, the authors have included advanced material that make it appropriate for postgraduate courses. The text discusses the chemical reactivity and synthesis of particular heterocyclic systems. Exercises and solutions help students understand and apply the principles. Original references are included throughout, as well as many review references.

Table of Contents

STRUCTURES AND MAIN PHYSICAL PROPERTIES OF AROMATIC Heterocycles

Carbocyclic Aromatic Systems

Structure of Six-Membered Heteroaromatic Systems

Structure of Five-Membered Heteroaromatic Systems

Structures of Bicyclic Heteroaromatic Compounds

Tautomerism in Heterocyclic Systems

Mesoionic Systems

Some Spectroscopic Properties of Some Heteroaromatic Systems

REACTIVITY OF AROMATIC HETEROCYCLES

Electrophilic Addition at Nitrogen

Electrophilic Substitution at Carbon

Nucleophilic Substitution at Carbon

Radical Substitution at Carbon

Deprotonation of N-Hydrogen

Organometallic Derivatives

Palladium-Catalysed Reactions

Oxidation and Reduction of Hetocyclic Rings

SYNTHESIS OF AROMATIC HETEROCYCLES

Reaction Types Most Frequently Used in Heterocyclic Ring Synthesis

Typical Reactant Combinations

Summary

Electrocyclic Processes in Heterocyclic Ring Synthesis

Nitrenes in Heterocyclic Ring Synthesis

TYPICAL REACTIVITY OF PYRIDINES, QUINOLINES, AND ISOQUINOLINES

PYRIDINES: REACTIONS AND SYNTHESIS

Reactions with Electrophilic Reagents

Reactions with Oxidising Agents

Reactions with Nucleophile Reagents

Reactions with Bases

Reactions with C-Metallated Pyridines

Reactions with Radical Reagents

Reactions with Reducing Agents

Eletrocyclic Reactiosn (Ground State)

Photochemical Reactions

Oxy-and Aminopyridines

Alkylpyridines

Pyridines Aldehydes, Ketones, Carboxylic Acids, and Esters

Quaternary Pyridinium Salts

Pyridine N-Oxides

Synthesis of Pyridines

QUINOLINES AND ISOQUINILINES: REACTIONS AND SYNTHESIS

Reactions with Electrophilic Reagents

Reactions with Oxidising Agents

Reactions with Nucleophilic Reagents

Reactions with Bases

Reactions of C-Metallated Quinolines and Isoquinolines

Reactions with Radical Reagents

Reactions with Radical Agents

Electocyclic Reactions (Ground State)

Photochemical Reactions

Oxyquinolines and -Isoquinolines

Aminoquinilines and -Isoquinilines

Alkylquinolines and -Isoquinolines

Quinoline and Isoquinoline Carboxylic Acids and Esters

Quaternary Quinoline and Isoquinoline Salts

Quinoline and Isoquinoline N-Oxides

Synthesis of Quinolines and Isoquinolines

TYPICAL REACTIVITY OF PYRYLIUM AND BENZOPYRYLIUM IONS, PYRONES, AND BENZOPYRONES

PYRYLIUMS, 2- AND 4-PYRONES: REACTIONS AND SYNTHESIS

Reactions of Pyrylium Cations

-Pyrones and -Pyrones

Synthesis of Pyryliums

Synthesis of -Pyrones

Synthesis of -Pyrones

BENZOPYRYLIUMS AND BENZOPYRONES: REACTIONS AND SYNTHESIS

Reactions of Benzopyryliums

Benzopyrones (Chromones, Coumarins, and Isocoumarins)

Synthesis of Benzopyryliums, Chromones, Coumarins, and Isocoumarins

TYPICAL REACTIVITY OF THE DIAZINES: PYRIDAZINE, PYRIMIDINE, AND PYRAZINE

THE DIAZINES: PYRIDAZINE, PYRIMIDINE, AND PYRAZINE: REACTIONS AND SYNTHESIS

Reactions with Electrophilic Reagents

Reactions with Oxidising Agents

Reactions with Nucleophilic Reagents

Reactions with Bases

Reactions with C-Metallated Diazines

Reactions with Reducing Agents

Reactions with Radical Reagents

Electrocyclic and Photochemical Reactions

Diazine N-Oxides

Oxydiazines

Aminodiazines

Alkydiazines

Synthesis of Diazines

Reactions with Bases: Reactions of C-Metallated Benz(b)thiophenes and Benxo(b)furans

Reactions with Reducing Agents

Oxy-and Amino-Benzothiopenes and Benzofurans

ISOINDOLES, BENZO[C]THIOPENES AND ISOBENZOFURANS: REACTIONS AND SYNTHESIS

Reactions with Electrophilic Reagents

Electrocyclic Reactions (Ground State)

Phthakicyanines

Synthesis of Isoindoles, Benzo[c]thiophenes and Isobenxofurans

TYPICAL REACTIVITY OF 1,3,- AND 1,2-AZOLES: REACTIONS AND SYNTHESIS

Reactions with Electrophilic Reagents

Reactions with Oxidising Agents

Reactions with Nucleophilic Reagents

Reactions with Bases

Reactions of N-Metallated Imidazoels

Reactions of C-Metallated 1,3-Azoles

Reactions with Reducing Agents

Electrocyclic and Photochemical Reactions

Alkyl-1, 3-Azoles

Quaternary 1,3-Azolium Salts

Oxy- and Amino-1,3-Azoles

Synthesis of 1,3-Azoles

1,2-AZOLES:PYRAZOLES, ISOTHIAZOLES, AND ISOXAZOLES: REACTIONS AND SYNTHESIS

Reactions with Electrophilic Reagents

Reactions with Oxidising Agents

Reactions with Nucleophilic Reagents

Reactions with Bases

Reactions of N-Metallated Pyrazoles

Reactions of C-Metallated 1,2-azoles

Reactions with Reducing Agents

Electrocyclic and Photochemical Reactions

Alkyl-1,2-Azoles

Quaternary 1,2-Azolium Salts

Oxy- and Amino-1,2-Azoles

PURINES: REACTIONS AND SYNTHESIS

Nucleic Acids, Nucleosides and Nucleotides

Reactions with Electrophiic Reagents

Reactions with Radical Reagents

Reactions with Oxidising Agents

Reactions with Reducing Agents

Reactions with Nucleophiic Agents

Reactions with Bases

Reactions with N-Metallated Purines

Reactions with C-Metallated Purines

Oxy- and Aminopurines

Alkylpurines

Purine Carboxylic Acids

Synthesis of Purines

HETEROCYCLES CONTAINING A RING-JUNCTION NITROGEN

Indolizines

Aza-Indolizines

Quinoliziniums and Related Systems

Pyrrolizines and Related Systems

Cyclazines

HETEROCYCLES CONTAINING MORE THAN TWO HETERO ATOMS

Five-Membered Rings

Six-Membered Rings

Saturated and Partially Unsaturated Heterocyclic Compounds: Reactions and Synthesis

Five- and Six-Membered Rings

Three-Membered Rings

Four-Membered Rings

Metallation

Ring Synthesis

Appendix: Answers to Exercises

Subject Categories

BISAC Subject Codes/Headings:
MED008000
MEDICAL / Biochemistry
SCI013000
SCIENCE / Chemistry / General
SCI013040
SCIENCE / Chemistry / Organic