Reaction of Aminopropanedinitrile 4-Methylbenzenesulfonate (Aminomalononitrile p-Toluenesulfonate (Tosylate)) with Isothiocyanates

Article abstract of DOI:10.1021/jo00015a015

Aminopropanedinitrile 4-methylbenzenesulfonate (ammoniopropanedinitrile or aminomalononitrile p-toluenesulfonate (tosylate)) reacts with alkyl and aryl isothiocyanates in 1-methyl-2-pyrrolidinone (NMP) to give 5-amino-2-(alkylamino)-4-cyanothiazoles and 5-amino-2-(arylamino)-4-cyanothiazoles (2,5-diaminothiazole-4-carbonitriles), respectively, which react with amidines or ortho esters to afford 7-amino-2-(alkylamino)thiazolo<5,4-d>pyrimidines and 7-amino-2-amino-2-(arylamino)thiazolo<5,4-d>pyrimidines.