Aminothiazoles and Their Derivatives (R. Barone et al.).
Mercaptothiazoles, Hydroxythiazoles and Their Derivatives (C. Roussel et al.).
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
Other examples of this reactivity are given in the tables (Section VII). Acetylation of 2-phenyl-4-amino-5-benzoylthiazoletakes place on the exocyclic nitrogen (49). Its acetylation with acetic anhydride gives the 4-acetamido derivative (112),which reacts further on heating to yield 2-(acetylimino)-(3H)3-aryl-5-methylthiazolo[4,5-d]pyrimidin-7-(6H)-one (113) (Scheme 76) (276). Boiling acetic acid converts 2-aminothiazole into the 2-acetamido derivative far more easily when catalytic amounts of diketene are added to the reaction mixture (277).
Alkylation of the sodium salt of 2-formamido-5-nitrothiazole(48) (R= H) O2N z l N"-COR * , O2N Z ' N c o R 488 - 48b Scheme 35 48c 37 111. ) yields a mixture of ring N and exocyclic N alkylation (192). Dyatlova (193) reports the preparation of product 49, resulting from the dialkylation of 2-aminothiazole with a-chloroacetic acid under mild conditions (Scheme 36). NH, +CH,ClCO,Na NaOH 40% Me,co s@ 3 \ 49 0"Na' Scheme 36 2-Nitraminothiazoles are sufficiently acidic to be alkylated by diazomethane; the methyl substituent is introduced on the exocyclic nitrogen (194).
Ultraviolet spectroscopy also differentiates these isomers (200). They can be separated by boiling in ethanol: the thiazoline isomer is usually far less soluble in this solvent (131). C. Acidic Medium Reactions of the 2-amino-4,5-substituted thiazole (52) in acetic acid with ethylene oxide has been reported to give the N-exocyclic disubstitution product (53) (201) in a 40% yield (Scheme 38). The reactive species in this reaction is probably the carbocation generated in acetic acid by ethylene oxide.