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Aminothiazoles and Their Derivatives (R. Barone et al.).

Mercaptothiazoles, Hydroxythiazoles and Their Derivatives (C. Roussel et al.).

topic Index.Content:
Chapter VI Aminothiazoles and Their Derivatives (pages 9–368): R. Barone, M. Chanon and R. Gallo
Chapter VII Mercaptothiazoles, Hydroxythiazoles and Their Derivatives (pages 369–560): Christian Roussel, Michel Chanon and Rene Barone

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Extra info for Chemistry of Heterocyclic Compounds: Thiazole and its Derivatives, Part Two, Volume 34

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Scheme 15 15b NN'-Dialkylamino derivatives were studied by Chouteau et al. (1 15). The main assignments are summarized in Table VI-4. Sheinker et al. thoroughly studied protomeric equilibria by a study of the infrared properties of 2-aminothiazole and 2-imino-4-thiazoline derivatives (94, 105, 119). His results confirm that the amino form is predominant, a conclusion also drawn from the infrared absorption study of 2-anilinothiazole (120) and 2-heteroarylaminothiazoles (1569). N-Methyl-2-acetamidothiazole is representative of the 2-aminothiazole structure, absorbing at 1542 and 1648 cm-'; its isomeric imino counter(16),has only one band at part, 2-acetylimino-3-methyl-4-thiazoline 1588 cm-'.

With an excess of chloroformate (2 moles for one of the thiazole) under Schotten-Bauman conditions the N,N’-dicarbamate of 2-imino-4-methylthiazoline (102)is obtained (263). Me XJ. Scheme 70 102 Chlorothioformic phenyl ester (103)reacts under mild conditions with 2-arninothiazole to give 104 (Scheme 71) (266). cl + PhOCSCl 2-% G N H C O P h NHZ II 103 Scheme 71 104 S 52 Aminothiazoles and their Derivatives b. REACTIONS WITH ACIDS AND THEIR ANHYDRIDES Acetic anhydride and sodium acetate when heated with 2aminothiazole for 2 hr give 2-acetamidothiazole 105 (Scheme 72) (243).

E. 2. Reactions witb Reagents Bearing an sfC Electrophilic Center A. Additions to C=C Nucleophilic addition of 2-aminothiazole to the double bond of dimaleic acid hydrazine has been reported (206). No spectroscopic proof, however, is given to establish the proposed structure (60)for the resulting product (Scheme 41). 2ThNH2 + {:-+ n = 2-thimlyl d + $ 60 NHTh Scheme 41 B. Reactions with CarbonyI Derivatives The exocyclic nitrogen atom is involved when 2-aminothiazoles and aromatic aldehydes react under mild conditions yielding 61 (Scheme 42) 61 R = Ph.

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