Am. Dias et al., SYNTHESIS OF NEW IMIDAZO[4,5-D][1,3]DIAZEPINE DERIVATIVES FROM 5-AMINO-4-(CYANOFORMIMIDOYL)IMIDAZOLES, Journal of heterocyclic chemistry, 33(3), 1996, pp. 855-862
N-1-[(Z)-2-Amino-1,2-dicyanovinyl]formamidines 1a-d react readily with
tosyl isocyanate to form novel ed-5-oxo-7-tosylaminoimidazo[4,5-d][1,
3]diazepines 6a-d rather than the 6-cyano-2-oxopurine derivatives 5a-d
expected. Compound 5a has been synthesized from 1a by reaction with e
thyl chloroformate and base-catalyzed cyclization of the resultant eth
oxycarbonylamino-4-(cyanoformimidoyl)imidazole. Treatment of the 5-ami
no-4-cyanoimidazoles 7a and b with tosyl isocyanate under similar cond
itions gives the 4-cyano-5-(3'-tosylureido)imidazoles 8a and b, which
on treatment with ethanolic ammonia cyclizes to the corresponding isog
uanines 10a and b.