Expeditious Routes to 4-Alkoxyquinazoline-2-carbonitriles and Thiocarbamates via N-Arylimino-1,2,3-dithiazoles Using Microwave Irradiation.

Abstract Conversion of N -arylimino-4-chloro-5 H -1,2,3-dithiazole 11 into the 4-alkoxyquinazoline-2-carbonitriles 13a-i and of the aryl isothiocyanates 15 into aryl thiocarbamates 16a-j with sodium alkoxides in the corresponding alcohol, either by conventional thermolysis or by microwave irradiation are described and directly compared. Microwave irradiation of the solutions in open vessels in a monomode system with focused irradiation and continuous temperature control (Synthewave S402 reactor) usually gave cleaner, faster and higher yielding reactions. These reactions could be safely and beneficially scaled up to multigram quantities in a larger reactor (Synthewave S1000).