Abstract
An expeditious and concise synthesis of highly congested 2-amino-3-aminomethyl-5-methylsulfanyl/- sec-aminobiphenyl-4-carbonitrile 4 and 1- tert-butoxycarbonyl-6- sec-amino-8-aryl-5-cyano-2- oxo-1,2,3,4-tetrahydroquinazoline 5 has been delineated through base catalyzed ring transformation of 6-aryl-4-methylsulfanyl/- sec-amino-2 H-pyran-2-one-3-carbonitrile 1 with 1,3-bis( tert-butoxycarbonylamino)-2-propanone 2, followed by TFA catalyzed hydrolysis of the intermediate [3- tert-butoxycarbonylaminomethyl-4-cyano-5-methylsulfanyl/- sec-aminobiphenyl-2-yl]carbamic acid tert-butyl ester 3 in moderate yield. The mechanism of formation of 5 has been established through isolation and transformation of the intermediate 3 to the 1- tert-butoxycarbonyl-6- sec-amino-8-aryl-5-cyano-2- oxo-1,2,3,4-tetrahydroquinazoline.
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