Reaction of Biguanides and Related Compounds. I. Reaction of Biguanides with β-Diketone

抄録

Biguanide derivatives were allowed to react with acetylacetone and benzoylacetone. Both of alkyl and arylbiguanides reacted with acetylacetone to give the corresponding 4, 6-dimethyl-2-alkyl or arylguanidinopyrimidine. On the other hand, arylbiguanides were found to exhibit chemical behaviors different from alkylbiguanides toward benzoylacetone. Two moles of arylbiguanides reacted with benzoylacetone to give 6-arylamino-4-amino-2-phenyl-2(6'-arylamino-4'-amino-2'-methyl-1', 2', -dihydro-s-triazinyl-2'-methyl)-1, 2-dihydro-s-triazine, though alkylbiguanides gave 6-methyl-4-phenyl-2-alkylguanidinopyrimidine under the similar condition. It was noted that the reaction of 1-methyl-1-phenyl-biguanide with benzoylacetone resulted in the formation of 6-methyl-4-phenyl-2-methyl-phenylguanidinopyrimidine without formation of any expected bisdihydro-s-triazine.