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Heterocyclic Chemistry, 3rd Edition

Edition:
3rd
Author(s):
John Joule, Keith Mills, George Smith
ISBN:
9780748740697
Format:
Paperback
Publication Date:
October 20, 1995
Content Details:
534 pages
Language:
English

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  • About the Book

    Book Summary

    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.

    Features

    • Provides detailed, systematic discussions of the chemical reactivity of particular heterocyclic systems such as pyridines, quinolines, and more
    • Explains heterocyclic principles in basic terms
    • Discusses radical substitution, metallation, and pallidium-catalysed reactions
  • 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