Reaction of dicyandiamide with thiosemicarbazide and thiocarbohydrazide: Formation of 1-Amino-4-imino(or arylimino)-6-imino(or hydrazono)hexahydro-1,3,5-triazine-2-thiones

Abstract

Dicyandiamide and aryldicyandiamides react with thiosemicarbazide to yield 1-amino-4-imino(or arylimino)-6-iminohexahydro-l,3,5-triazine-2-thiones. Acid hydrolysis of these compounds results in 3-amino-5-amino(or ary1amino)-1,2,4-triazoles with loss of thiocyanic acid, and their condensation with phenacyl bromide yields 8-amino(or arylamino)-6-imino-3-phenyl-4H,6H-[1,3,5]triazino-[2,1-b][1,3,4]thiadiazines.Reaction of thiocarbohydrazide with dicyandiamides affords 1-amino-4-imino(or ary1imino)-6-hydrazonohexahydro-l,3,5-triazine-2-thiones. These compounds are converted into 8-amino(or arylamino)-6-hydrazono-3-phenyl-4H,6H-[l,3,5]triazino-[2,l-b][1,3,4]thiadiazines by treatment with phenacyl bromide.