Synthesis of Furan Derivatives. XIV. Synthesis of β-(5-Nitro-2-furyl)-α-methyl-, -α-ethyl-, and -α-bromo-acrolein Derivatives

Abstract

β-(5-Nitro-2-furyl)-α-methylacrolein and β-(5-nitro-2-furyl)-α-ethylacrolein were prepared by the condensation of 2-(5-nitro) furfural with propionaldehyde and butyraldehyde, respectively, in the presence of piperidinium acetate as a catalyst. Preparation of β-(5-nitro-2-furyl)-α-bromoacrolein was accomplished by bromination in the usual manner. These new compounds were used as an antibacterial group in the preparation of Schiff bases with semicarbazides, hydrazides, and amines, and then antibacterial screening of these bases was carried out. From the screening results, β-(5-nitro-2-furyl)-α-methylacrolein semicarbazone, β-(5-nitro-2-furyl)-α-methylacrolein oxime, and 1-[β-(5-nitro-2-furyl)-α-bromoacrylidene]-2-isonicotinylhydrazine were found to exert great activity against tubercle bacilli.