Thiazolo]3,2-a[-1,3,5-triazines. Preparation of 4-substituted 2-thiazolyl isothiocyanates and their reactions with isocyanates, aldimines and carbodiimides

Abstract

4-(Methyl- or phenyl)-2-thiazolyl isothiocyanates were synthesized from the appropriate amine hydrochlorides by thiophosgene method. The [4 + 2] cycloaddition reaction of 4-methyl-2-thiazolyl isothiocyanate with isocyanates and aldimines afforded thiazolo[3,2-a]-1,3,5-triazine derivatives. 4-Phenyl-2-thiazolyl isothiocyanate on the other hand, did not react with isocyanates. Carbodiimides were found to react with 4-methyl-2-thiazolyl isothiocyanate by a [2 + 2] cycloaddition to yield the substituted 1,3-thiazetidines.