An EFFICIENT SYNTHESIS OF Β-(3-Quinolinyl)-Α-Alanine

Abstract

A convenient synthesis for β-(3-quinolinyl)-α-alanine (4) is presented. Condensation of 2-chloro-3-chloromethylquinoline (5) with diethyl acetamidomalonate (2) gave high yield of diethyl 2-acetylamino-2-(2-chloro-3-quinolinylmethyl)- propanedionate (6), which was dehalogenated in the presence of ammonium formate and palladium/charcoal. Diethyl 2-acetamido-2-(3-quinolinylmethyl)-malonate (3) was easily converted to the amino acid. The condensation reaction between 2 and 6 is also useful for the construction of (1H)-2,3-dihydropyrrolo[2,3-b]quinoline-2,2-bis(carboxylic acid) and pyrrolo[2,3-b]quinoline-2-carboxylic acid derivatives.