Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center , Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran, I.R. IRAN
A new, high yielding method for the preparation of vasicinone (7) is described. Reaction of 2-nitrobenzoic acid with N, N¢-carbonyldiimidazole followed by 2-pyrrolidinone gave 1-(2-nitrobenzoyl)pyrrolidine-2-one (3). Reduction of the latter with 10% Pd-C afforded deoxyvasicinone (4). Reaction of deoxyvasicinone (4) with bromine yielded monobromo-deoxyvasicinone (5). Exchange of bromine of 5 with acetoxy followed by hydrolysis gave vasicinone in high yield.