3- dimethylamino-2-isocyanoacrylic acid methyl

Aminothiocarboxylic acids react with aldehydes and 3-dimethylamino-2-isocyanoacrylic acid methyl ester following the pathway described for /7-aminoacids, affording, after ring contraction of the seven-membered intermediate 87, Michael-type cyclization and /7-elimination, /7-lactam 88 equipped with a thiazole... 

A (3-lactam ring substituted by a thiazole moiety has been reported to be formed simultaneously and under mild condition during the course of a multicomponent reaction [200]. When the 3-dimethylamino-2-isocyanoacrylate was reacted with the aldehyde in the presence of a (3-aminothiocarboxylic acid, substituted l-thiazole-2-yl-methyl-azetidin-2-one was smoothly formed (Scheme 92). Plausible reaction intermediates have been proposed. 

Other similar methods which involve cyclization of iV-substituted diaminoalkenes or -alkanes include the preparation of 2-alkyl- and 2-acyl-l-methylimidazole-4-carboxylates from methyl (Z)-j -dimethylamino-a-isocyanoacrylate (191) in reaction with an alkyl or acyl halide <82LA2093>, the preparation of perfluorinated 3-imidazolines (192) <83S169>, the high yield synthesis of 2-imidazolines by decay of phosphaza compounds (193) in a version of the intramolecular Staudinger reaction <85T793>, and the formation of 1,3-diaroylimidazolidines (34-71%) when bis-alkylidene-or -arylidene-ethylenediamines react with acid chlorides in polar solvents (Scheme 129)... 

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