Pyrimidine Derivatives. X. Synthesis of New Tricyclic Hetero Compounds Possessing a Pyrimidine Ring : 8, 1, 3, 10-Thiatriazatricyclo[4.3.0.0^{6, 10}]-dodecanes and 8, 1, 3, 10-Thiatriazatricyclo[4.4.0.0^{6, 10}]tridecanes

Abstract

Several new tricyclic hetero compounds possessing a pyrimidine ring were formed by reaction of 5-bromo- (and 5-nitro)-1-(2-bromoethyl, 3-bromopropyl, and 2-bromopropyl)-6-bromomethyl-3-methyl-2, 4(1H, 3H)-pyrimidinediones (1a-c and 7a, b) with thiourea derivatives : namely, 5-bromo-(and-5-nitro)-9-imino-3-methyl-(and 3, 11-dimethyl)-2, 4-dioxo-8, 1, 3, 10-thiatriazatricyclo[4.3.0.0^{6, 10}]dodecanes (2a-4a, 2c, and 8a-10a) and 5-bromo-(and 5-nitro)-9-imino-3-methyl-2, 4-dioxo-8, 1, 3, 10-thiatriazatricyclo[4.4.0.0^{6, 10}]tridecanes (2b-4b and 8b-10b). A new ring transformation reaction was found : compound 8b was converted to 7-acetylimino-3-methyl-2, 4-dioxo-6, 1, 3, 8-thiatriazatricyclo-[4.4.0.1^{5, 8}]dodec-5(12)-ene (11) by reaction with acetic anhydride.