Abstract
The reaction of arylbiguanide with carboxylic esters having a reactive functional group except the ester group such as ethyl cyanoacetate, ethyl acetoacetate and diethyl oxalate was attempted. Roy et al. inferred that the reaction product of arylbiguanide with ethyl cyanoacetate should be 2-arylguanidino-6-amino-4-pyrimidinol. Contrary to the Roy's result, however, the author proved that it might be 4-amino-6-arylamino-striazine-2-acetonitrile. In comparison with this fact, the reaction of 1-arylbiguanide with ethyl acetoacetate was confirmed to afford 2-arylguanidino-6-methyl-4-pyrimidinol under the similar reaction condition. Furthormore, the author defined the reaction mechanism in which 1-arylbiguanide reacts with diethyl oxalate to give ethyl 4-amino-6-arylamino-s-triazine-2-carboxylate through the intermediate formation of 1-aryl-3-(4, 5-dioxo-2-imidazolidinylidene)-guanidine. In connection with this finding, 4-amino-6-(p-toluidino)-s-triazine-2-carboxamide derivatives was found to be formed by the reaction of 1-(p-tolyl)-3-(4, 5-dioxo-2-imidazolidinylidene)-guanidine with corresponding amine. Therefore it is recommended to be a new method of synthesizing 4-amino-6-arylamino-s-triazine-2-carboxamides from 1-arylbiguanide, diethyl oxalate and an amine.
