Reduction of Isopropylidene Acylmalonates, 5-Acylbarbituric Acids, and 3-Acyl-4-hydroxycoumarins to the Corresponding Alkyl Derivatives by Sodium Cyanoborohydride-Acetic Acid

Article abstract of DOI:10.1021/jo01311a011

Isopropylidene acylmalonates, 5-acylbarbituric acids, and 3-acyl-4-hydroxycoumarins are readily reduced to the corresponding alkyl derivatives by sodium cyanoborohydride-acetic acid.The cyclic substrates are readily prepared by the acylation of isopropylidene malonate, barbituric acid (or its N,N'-dimethyl derivative), and 4-hydroxycoumarin, according to procedures developed by other workers.The reductions take place upon addition of a 2 mol equiv of sodium cyanoborohydride to a mixture of the acyl compound and acetic acid.This reductive transformation completes a synthetic method for the preparation of the alkyl derivatives starting from the parent compound.