Thiazole and its Derivatives. Part Three

Автор(ы):Metzger J. V.
06.10.2007
Год изд.:1979
Описание: Given their theoretical as well as practical interest, five-membered aromatic rings occupy a position of particular significance in the enormous field of heterocyclic chemistry. Thiazole is one of the important members of this family and thus merits a comprehensive study. The purpose of this book is to condense into a volume of reasonable size the chemistry of thiazole, covering the literature of approximately one century, up to December 1976. For technical reasons this work has been limited to the study of monocyclic thiazoles, excluding thiamine and partially reduced thiazoles, but including selenazoles. Though most of the important material has been published in the last twenty years, all the literature concerning thiazoles has been surveyed, and it is of special interest to see with what energy Arthur Hantzsch was obliged to defend his historical discovery of thiazole.
Оглавление:
Thiazole and its Derivatives. Part Three — обложка книги.
Contents PART THREE
VIII. Mesoionic Thiazoles [1]
  M. BEGTRUP and C. ROUSSEL
IX. Cyanine Dyes Derived from Thiazolium Salts [23]
  H. LARIVE and R. DENNILAULER
X. Selenazole and Derivatives [217]
  R. GUGLIELMETTI
Subject Index [279]
Cumulative Author Index [295]

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. VERNIN
III. Alkyl. Aryl, Aralkyl aud Related Thiazole Derivatives
  J. P. AUNE, H. J. M. DOU, and J. CROUSIER
IV. Ibiazolecarboxylic Acids, Thiazolecarboxaldehydes, and Thiazolyl Ketones
  R. MEYER
V. Halo- and NHrothiazoles
  L. FORLANI and P. E. TODESCO Subject Index

PART TWO
General Introduction to Protomeric Thiazoles
  M. CHANON
VI. Aminothiazoles and their Derivatives
  R. BARONE, M. CHANON, and R. GALLO
VII. Mercaptothiazoles, Hydroxyihiazoles and their Derivatives
  C. ROUSSEL, M. CHANON, and R. BARONE
Subject Index

VIII. Mesoionic Thiazoles
MIKAEL BEGTRUP
The Technical University of Denmark, Department of Organic Chemistry Lyngby, Denmark and CHRISTIAN ROUSSEL
Inslirar de Pemlcochimie et de Synthcse Organique IndusUrielle Vnioersitc d'Aix-Marseille III Marseille, France
  I. Introduction [1]
  II. 4-Hydroxythiazolium Hydroxide Inner Salts [4]
  III. 4-Aminothiazolium Hydroxide Inner Salts [8]
  IV. 4-Mercapto- or 4-Alkylidenethiazolium Hydroxide Inner Salts [8]
  V. 5-Hydroxythiazolium Hydroxide Inner Salts [8]
  VI. 5-Mercaptothiazolium Hydroxide Inner Salts [12]
  VII. 5-Aminothiazolium Hydroxide Inner Salts [13]
  VIII. 5-Alkylidenethiazolium Hydroxide Inner Salts [15]
  IX. Tables of Compounds [16]
  X. References [20]
IX. Cyanine Dyes Derived from Thiazolium Salts
HENRI LARIVE and RENE DENNILAULER
Kodak-Pathe Research Laboratories, Vincennes, France
  I. Nomenclature [25]
  II. Thiazolium Quaternary' Salts [30]
    1. Electrophilic Properties of Thiazolium Salts [32]
    2. Specific Behavior of 2-Methylthiazolium Salts in Basic Medium [36]
      A. Anhydrobases [37]
      B. Mechanism of Thiazolocyanine Formation from Anhydrobases [40]
      C. Obtention of Neutrocyanine from Anhydrobases [47]
  III. Syntheses of Thiazolocyanines [48]
    1. Mononuclear Cyanines [48]
      A. Hemicyanines [48]
      B. Styryl Dyes [49]
      C. Dimethine Cyanines [51]
      D. Azastyryl Dyes [51]
      E. Nonionic Mononuclear Compounds [51]
    2. Dinuclear Cyanines [52]
      A. Cationic Dyes [52]
        a. Monomethine Thiazolocyanines [52]
        b. Trimethine Thiazolocyanines [54]
        c. Pentamethine Thiazolocyanines [56]
        d. Heptamethine Thiazolocyanines [57]
        e. Chain-Bridged Thiazolocyanines [58]
        f. Azacyanines [58]
      B. Neutrocyanines (or Merocyanines) [59]
        a. Zeromethine Cyanines [59]
        b. Dimethine Neutrocyanines [60]
        c. Tetramethine Neutrocyanines [63]
        d. Hexamethine Neutrocyanines [63]
        e. Azaneutrocvanines [64]
    3. Trmuclear Dyes [64]
      A. Rhodacyanines [64]
      B. Neocyanines [65]
    4. Teiranuclear Dyes [68]
  IV. Structure and Color [68]
    1. Resonance Theory and Concept of "Basicity" [68]
    2. Limit of the "Basicity" Concept [71]
    3. Modern Conception [72]
    4. Absorption and Substituents [75]
      A. Influence of Substituents in the Nuclei [75]
      B. Substituems op the Chain [77]
      C. Nitrogen Atoms Replacing Methine Groups of the Chain [78]
  V. Uses of Dyes [78]
    1. Photography [78]
    2. Textile Dyes [80]
    3. Pharmaceutical Uses [80]
  VI. List of Thiazolium Salts [81]
  VII. Classification and List of Thiazolocyanine Dyes [99]
  VIII. References [197]
X. Selenazole and Derivatives
ROBERT J. GUGLIELMETTI
Universite de Bretagne Occidentals Brest, France
  I. Introduction [218]
  II. General Preparative Methods of Selenazoles [219]
    1. Substituted Alkyl and Arylselenazoles [219]
    2. Substituted 2-Aminoselenazoles [222]
      A. Synthesis from Selenourea [222]
      B. Synthesis from N'-substituted Sclenoureas [225]
      C. Synthesis from N-acyl Selenoureas [230]
      D. General Properties [230]
    3. 2-Hydrazinoselenazoles and 2-Isopropyhdenehydrazino or 2-Benzylidene-hydrazinoselenazoles [232]
    4. Other Functional Derivatives, of Selenazole [236]
      A. Thioethers [236]
      B. 2-Mercaptoselenazoles [237]
      C. Synthesis of 2-(2- or 4-furyl. thienyl, or selenienyllselenazoles [237]
  III. Reactivity of the Selenazole Ring and of Derived Compounds [239]
    1. Electrophilic Substitution Reactions [241]
      A. Nitration [241]
      B. Sulfonation [243]
      C. Halogenation [243]
      D. Diazo Coupling [246]
      E. Nitrosation [246]
    2. Sulfanilamidoselenazoles [248]
    3. Condensation with Carbonyl Derivatives [249]
    4. Condensation of Selenated Alkylidene or Benzylidene Hydrazones or Pyrazolones with p-nitroso Dialkylanilines [250]
      A. Isopropylidene and Benzylidene Hydrazones [250]
      В. 2-Pyrazoloneselenazoles [252]
    5. Oxidation to Quinoid Dyes [252]
    6. belenazoleformazans [254]
    7. Quaternary Salts [256]
    8. Reactivity of 2-Amino Selenazoles with Ethyl Propiolate and Dimethyl Acetylene Dicarboxylatc [257]
  IV. Other Heterocycles Directly Derived from Selenazole [258]
    1. Selenazolines [258]
      A. Alkyl or An4-ArSelenazolines [258]
      B. 2-Amino-(?)-Selenazolines [259]
      C. 4-Oxo-Disubstituted 2-Amino-(?)-(?)-Selenazolines [261]
      D. 2-Acyl-A4-Selenazolines [264]
    2. Selenazolidines [265]
      A. Alkyl or Arylbelenazolidines [265]
      B. 2-Iminoselenazolidin-4-ones. Selenazolidin-2,4-diones and 2-Arylidene-hydrazones [269]
      C. 2-Thio-4-oxoselenazolidineb [272]
  V. Physicochemical Studies [272]
    1. Infrared [272]
      A. Methylselenazoles [272]
      B. Substituted Selenazolidinediones (and their sulfur and oxygen homoloesi [273]
      C. 2-Thio-4-oxoselenazolidines (and their oxygen, sulfur, and nitrogen homologs) [274]
    2. Ultraviolet Spectroscopy [274]
    3. NMR and Mass Spectrometry [274]
  VI. Applications of Selenium Heterocycles [274]
    1. Dyes [274]
    2. Biological Activity and Radioprotection [275]
  VII. Conclusion [275]
  VIII. References [276]
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