Heterocyclic Chemistry, 3rd Edition  book cover
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3rd Edition

Heterocyclic Chemistry, 3rd Edition




ISBN 9780748740697
Published October 20, 1995 by CRC Press
534 Pages

 
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Book 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

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