Collect. Czech. Chem. Commun. 1984, 49, 1788-1794

Preparation and reactions of 2-amino-3-cyano-4,5-bis(3,4-methylenedioxybenzyl)furan

Josef Prousek

Department of Environmental Chemistry and Technology, Slovak Institute of Technology, 812 37 Bratislava


Treatment of 2-hydroxy-1,4-bis(3,4-methylenedioxyphenyl)-3-butenone with propanedinitrile (I) catalyzed by diethylamine afforded 2-amino-3-cyano-4,5-bis(methylenedioxybenzyl)furan (II). The latter reacted with formamide to 4-amino-5,6-bis-(3,4-methylenedioxybenzyl)furo[2,3-b]-pyrimidine (III), and with aldehydes to the corresponding azomethines IVa-IVe. The structure of products was adduced from spectral (IR, UV, 1H NMR, and mass) data. The inhibition of incorporation of [U14C]-L-valine for DNK synthesis and proteosynthesis of leukemia P-388 cells was tested with derivatives II and III.