New PDF release: Chemistry of Heterocyclic Compounds: Thiazole and Its

By Metzger

ISBN-10: 0470187085

ISBN-13: 9780470187081

ISBN-10: 0471039934

ISBN-13: 9780471039938

Houses and Reactions of Thiazole (J. Metzger and E. Vincent).

normal man made tools for Thiazole and Thiazolium Salts (G. Vernin).

Alkyl, Aryl, Aralkyl, and comparable Thiazole Derivatives (J. Aune et al.).

Thiazolecarboxylic Acids, Thiazolecarboxaldehydes, and Thiazolyl Ketones (R. Meyer).

Halo and Nitrothiazoles (L. Forlani and P. Todesco).

topic Index.Content:
Chapter I houses and Reactions of Thiazole (pages 5–164): Jacques V. Metzger, Emile?Jean Vincent, Jacques Chouteau and Gilbert Mille
Chapter II common man made tools for Thiazole and Thiazolium Salts (pages 165–335): Gaston Vernin
Chapter III Alkyl, Aryl, Aralkyl, and comparable Thiazole Derivatives (pages 337–518): Jean Pierre Aune, Henri Jean?Marie Dou and Jacqueline Crousier
Chapter IV Thiazolecarboxylic Acids, Thiazolecarboxaldehydes, and Thiazolyl Ketones (pages 519–563): Roger Meyer
Chapter V Halo? and Nitrothiazoles (pages 565–585): L. Forlani and P. E. Todesco

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Additional info for Chemistry of Heterocyclic Compounds: Thiazole and Its Derivatives, Part One, Volume 34

Sample text

C. Rhodanine In 1877, Nencki (22) condensing ammonium thiocyanate with chloroacetic acid, attributed the name rhodaninic acid (Rhodanindure) to the compound he obtained. H e noted the ability of rhodaninic acid to give colored derivatives with ferric salts. In 1879, Liebermann and Lange (20) demonstrated the formula of rhodaninic acid to be 39. In 1884, Nencki (70), studying the properties of rhodaninic acid, confirmed the formula proposed by Libermann and Lange (39) and noted its ability to condense with aldehydes.

Thiazole was also formed in the course of a study on the ease of decarboxylation of the three possible monocarboxylic acids derived from it (109). On the other EtO-CHCl I CH,CI OEt + N=C-S 8 \ 0 Scheme 43 hand, Asinger et al. (cf. Chapter 11) developed a general method of dehydrogenation of A-3-thiazolines that, applied to A-3-thiazoline itself, led to thiazole. More recently thiazole was obtained by photorearrangement of isothiazole (110). Various isotopically labeled thiazoles have been synthezised for physicochemical purposes: 2- and 5-deutero and 25 I.

Schemc 34 61 Properties and Reactions of Thiazole 22 In 1892, Marchesini (94) described the synthesis of 4-phenyl-2mercaptothiazole (62) by condensing bromoacetophenone with ammonium dithiocarbamate. Scheme 35 62 In 1893, Miolati (95) generalized the reaction of Marchesini to a halocarbonyl compounds. In 1896, Gabriel and Freiherr von Hirsch (96) condensed CS, with what they believed to be I-aminopropylene (2-methylaziridine) and obtained isomeric 4- and 5-methyl-2-mercaptothiazoline (63 and 64).

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