Thiazole and its Derivatives. Part Two

Автор(ы):Metzger J. V.
06.10.2007
Год изд.:1979
Описание: In the first chapter, devoted to thiazole itself, specific emphasis has been given to the structure and mechanistic aspects of the reactivity of the molecule: most of the theoretical methods and physical techniques available to date have been applied in the study of thiazole and its derivatives, and the results are discussed in detail The chapter devoted to methods of synthesis is especially detailed and traces the way for the preparation of any monocyclic thiazole derivative. Three chapters concern the non-tautomeric functional derivatives, and two are devoted to amino-, hydroxy- and mercaptothiazoles: these chapters constitute the core of the book.
Оглавление:
Thiazole and its Derivatives. Part Two — обложка книги.
PART TWO
General Introduction to Protomeric Thiazoles [1]
  M. CHANON
VI. Aminothiazoles and their Derivatives [9]
  R. BARONE. M. CHANOK. and R. GALLO
VII. Mercaptothiazoles, Hydroxythiazoles and their Derivatives [369]
  C. ROUSSEL, M. CHANON, and R. BARONE
Subject Index [561]

PART ONE
Introduction
I. Properties and Reactions of Thiazole
  J. V. METZGER. and E. J. VINCENT, with the collaboration of J. CHOUTEAU and G. MILLE
II. General Synthetic Methods for Thiazole and Thiazolium Salts
  G. VERNIK
III. Alkyl, Aryl, Aralkyl and Related Thiazole Derivatives
  J. P. AUNE. H. J. M. Dou, and J. CROUSIER
IV. Thiazolecarbovylic Acids, Thiazolecarboxaldehydes. and Thiazolyl Ketones
  R. MEYER
V. Halo- and Nitrothiazoles
  L. FORLANI and P. E. TODESCO
Subject Index

PART THREE
VIII. Mesoionic Thiazoles
  M. BEGTRUP and C. ROUSSEL
IX. Cyanine Dyes Derived from Thiazoliura Salts
  H. LARTVE and R. DENNILAULER
X. Sdenazole and Derivatives
  R. GuGLIELMETTl
Subject Index
Cumulative Author Index

VI. Aminothiazoles and their Derivatives
R. BARONE
Institui de Petnleochimie et de Synthese Organique Industrielle, Faculte des Sciences et Techniques de Saint-Jerome. Marseille, France.
M. CHANON
LA. 126 Faculte Sciences et Techniques de Saint Jerome, Marseille, France.
R. GALLO
Insfirur de Petroleochimie et de Synthese Organique Industrielle, Faculte des Sciences et Techniques de Saint-Jerome, Marseille, France.
  I. Synthesis from Preformed Thiazole Rings or from Other Heterocycles [11]
    1. 2-Aminothiazoles [12]
      A. Chichibabin Reaction [12]
      B. Ammonolysis of 2-Halothiazoies [12]
      C. Replacement of a Mercapto Group [13]
      D. Miscellaneous Reactions [13]
      E. Preparation of Secondary and Tertiary Amines [13]
    2. 4-Aminothiazoles [15]
    3. 5-Aminothiazoles [16]
  II. Spectroscopic and Physicochemical Properties [17]
    1. Molecular Orbital Calculations [17]
    2. pKa and Protomeric Equilibrium [18]
    3. Ultraviolet Spectroscopy and Photoelectron Spectroscopy [21]
    4. Infrared Spectroscopy [23]
    5. Nuclear Magnetic Resonance Spectroscopy [25]
    6. Mass Spectroscopy [27]
    7. Other Physical Methods [29]
    8. Analytical Methods [30]
  III. Nitrogen Reactivity [30]
    1. Substitution Reactions toward sp3C Electrophilic Centers [32]
      A. Weakly Acidic and Neutral Medium [32]
      B. Basic Medium [34]
      C. Acidic Medium [38]
    2. Reactions with Reagents Bearing an sp2C Electrophilic Center [40]
      A. Additions to C=C [40]
      B. Reactions with Carbonyl Derivatives [40]
      C. Reactivity toward Carbocations [47]
      D. Acylations [47]
      E. "Substitution Reactions on Aromatic sp2C [56]
    3. Reactions with Reagents Bearing an spC Electrophilic Center [57]
      A. Reactions with Isocyanates and Isothiocyanates [58]
      B. Reactions with Carbon Suboxide (O=C=C=C=O) [60]
      C. Reactions with Carbon Disulfide [60]
      D. Reactions with Ambident Electrophilic Reagents bearing an spC Electrophilic Center [61]
    4. Electrophilic Centers Other than Carbon [65]
      A. Nitrogen [65]
      B. Silicon [68]
      C. Phosphorus [68]
      D. Sulfur [69]
      E. Transition Metals [70]
    5. Rearrangements Involving Nitrogen [70]
  IV. Ring Carbon Reactivity [71]
    1. Reactivity toward Electrophilic Reagents [71]
      A. Nitration and Nitrosation [72]
      B. Sulfonation [75]
      C. Coupling with Diazonium Salts [76]
      D. Halogenation [77]
      E. Alkylation [80]
      F. Aminoalkylation [81]
      G. Mercuration [81]
      H. Rearrangements [82]
    2. Reactivity toward Nucleophilic Reagents [84]
  V. Aminothiazole Derivatives [90]
    1. N—C(X)R Subsiituenb [90]
      A. Acylamino Derivatives (X=O:R=alkyl, aryl) [90]
      B. Thiazolyl Ureas and Thioureas (X=O,S:R=NR3) [92]
      C. Thiazolyl Carbamates and Dithiocarbamates (X=O,S:R=OR.SR) [96]
      D. Thiazolyl Guamdines (X=NH:R=NHR) [97]
    2. Schiff Bases Derived from Aminothiazoles [98]
    3. 2-Hydrazinothiazoles [99]
    4. 2- and 5-Azothiazoles [105]
    5. 2-Thiazolyldiazonium Salts [109]
    6. 2-Nitraminothiazoles [112]
    7. 2-Azidothiazoles [113]
    8. Sulfenylthiazoles [113]
    9. Sulfonamidothiazoles [114]
    10. 2-Aminothiazole N-Oxides [118]
    11. Complexes of 2-Aminothiazoles with Metals [119]
    12. 2-Imino-4-thiazolines [122]
  VI. Applications of Aminothiazoles [132]
    1. Agricultural Applications [132]
    2. Pharmaceutical Uses—Toxicity [138]
    3. Analytical Uses [153]
    4. Dyes [154]
    5. Photography and Related Uses [154]
    6. Miscellaneous [154]
  VII. Tables of Compounds [171]
    1. General Organization of Tables of Compounds [171]
  VIII. References [319]
VII. Mercaptothiazoles, Hydroxy-thiazoles and their Derivatives
CHRISTIAN ROUSSEL
Institut de Petnleochime et de Synthese Organique Industrielle, Universite d'Aix-Marseille lit, Marseille, France
MICHEL CHANON
Faculte Sciences, St Jerome, Marseille, France
RENE BARONE
Institut de Petroleochmie et lie Synthese Organique Industrielle, Si Jerome, Marseille, France
  I. 2-Subsmuted Thiazoles [370]
    1. A-4-Thiazoline-2-thiones and A-4-Thiazoline-2-ones [370]
      A. Preparations (except Heterocyclization Methods,) [370]
      B. Physical Properties. Structures, and Analysis [377]
      C. Reactivity [391]
    2. Derivatives of (?)-4-Thiazoline-2-Thiones and (?)-4-Thiazoline-2-Ones [403]
      A. Thioethers and Ethers [403]
      B. Sulfenamides and Disulfides [411]
      С Sulfonic and Sulfinic Acids and Derivatives [413]
  II. 4- and 5-Substituted Thiazoles [416]
    1. Sulfur Derivatives [416]
      A. (?)-2-Thiazoline-4-Thione [416]
      B. (?)-2-Thiazoline-5-Thione [416]
    1. Oxygen Derivatives [419]
      A. (?)-2-Thiazoline-4-One and Derivatives [419]
      B. (?)-2-Thiazoline-5-One and Derivatives [426]
  III. Uses of Hydroxy and Mercapto Derivatives [436]
  IV. Tables of Compounds [443]
  V. References [536]
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