Synthesis of furan-3-carbonitriles by cyclization of cyano-substituted α,β-enones with potassium dinitromethanide

Abstract

A catalyst-free synthesis of furan-3-carbonitriles by cyclization of 2-arylidene-3-ketonitriles with potassium dinitromethanide was developed. Depending on the reagent ratio, this reaction afforded tri- and tetrasubstituted products. In the case of alkyl-substituted 2-arylidene-3-ketonitriles, the reaction diastereoselectively produced trans-5-nitro-4,5-dihydrofuran-3-carbonitriles.