Collect. Czech. Chem. Commun. 1980, 45, 1581-1588

Reactions and spectral properties of 2-amino-3-cyano-4,5-disubstituted furane derivatives

Josef Prousek, Adolf Jurášek and Jaroslav Kováč

Organic Chemistry Department, Slovak Institute of Technology, 880 37 Bratislava


Propanedinitrile reacts with acyloins I-III to give 2-amino-3-cyano-4,5-disubstituted furanes IV-VI; the latter react with formamide to give 4-amino-5,6-disubstituted furo[2,3-b]oyrimidines VII-IX. The derivative IV reacts with acetanhydride to 2-acetylamino-3-cyano-4,5-di(2-furyl)furane (X), and aminofurane VI reacts with acetanhydride to give 2-(N,N-diacetylamino)-3-cyano-4,5-diphenylfurane (XI). With aldehydes the aminofuranes IV-VI form the corresponding azomethines XII-XIV. The synthesized derivatives were identified by IR, UV, 1H-NMR and mass spectra.