The Journal of Organic Chemistry

Utility of p-nitrophenyl 3-bromo-2, 2-diethoxypropionate (NPBDP) in heterocyclic synthesis

JL LaMattina, CJ Mularski

Index: LaMattina, John L.; Mularski, Christian J. Journal of Organic Chemistry, 1984 , vol. 49, # 25 p. 4800 - 4805

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Citation Number: 39

Abstract

p-Nitrophenyl3-bromo-2, 2-diethoxyropionate (NPBDP, 3) reacts with a variety of nucleophiles at the activated ester to afford the corresponding 3-bromo-2, 2- diethoxypropionylated derivatives. With bifunctional nucleophiles, propionylation can be followed by intramolecular cyclization to give cyclic products. The a-bromo ketone moiety of the propionylated derivative can be liberated by heating at 85 OC in 95% formic acid. The ...