Studies on Antitumor Substances. VIII. Syntheses of 4-Amino-6-substituted Amino-2-substituted sym-Triazine Derivatives

Abstract

In order to synthesize a variety of 4-amino-6-substituted amino-2-substituted symtriazine, 1-substituted biguanide was allowed to react with ethyl chloroacetate to give 4-amino-6-substituted amino-2-chloromethyl-sym-triazine, from which the purpose compounds were derived. The reactions of 4-amino-6-substituted amino-2-chloromethyl-symtriazine with amines and alkylthiols were successfully carried out to give 4-amino-6-substituted amino-2-substituted aminomethyl-sym-triazine and 4-amino-6-substituted amino-2-alkylthiomethyl-sym-triazine, respectively. However, in the reaction with sodium alkanethiosulfonate, it was found to result in the formation of the corresponding sulfone afforded by the partial desulfurization in the intermediately formed 4-amino-6-substituted amino-2-methoxythiosulfonyl-sym-triazine. This sulfone was confirmed to be identical with that obtained by oxidation of the corresponding sulfide. The mercaptylation of 4-amino-6-piperidino-2-chloromethyl-sym-triazine with thiourea was resulted in the formation of the corresponding disulfide rather than the thiol compound anticipated.