Preparation and Spectral Properties of Novel N,S-Substituted Trichloronitrodienes

Abstract

The S-substituted nitrodienes were obtained by the reactions of polyhalo-3-nitrobutadiene 1 with some S-nucleophiles [4-(tert-butylbenzyl) thiol, 4-chlorophenylthiol, ethylthiol, and cyclopentylthiol] in directly at room temperature. N, S-Substituted trichloronitrodienes were synthesized from the reactions of the S-substituted nitrodienes with some piperazines in dichloromethane at room temperature. Their structures were characterized by microanalysis, Fourier transform infrared spectroscopy (FT-IR), H-1 nuclear magnetic resonance (H-1 NMR), C-13 nuclear magnetic resonance (C-13-NMR) and mass spectrometry (MS). The high temperature NMR technique was used for determination of methylene protons of piperazine ring in the new compound [4-(1-(2furoyl) piperazin-1-yl]-4-(4-tertbutylbenzyl-sulfanyl)-polyhalo-3-nitro-1,3-butadiene at 45 degrees C and 100 degrees C in DMSO.