Synthesis of Some Novel Thiazole, Thiophene, Thienopyridine and Thienopyrimidine Derivatives Containing Tosyl Moiety

Abstract

Interaction of 4-aminoacetophenone (1) with p-tolyl sulphonamide afforded 1-[4-tosyl amino) phenyl]ethanone (2).Treatment of 2 with bromine water yielded 2-bromo-1-[4-tosyl amino) phenyl]ethanone (3), which reacted with thiourea to give 2-amino thiazole derivative (4). Compound 2 was condensed with phenyl acetaldehyde and malononitrile to give derivatives ( 5) and ( 7), which were respectively reacted with o-aminothiophenol and carbon disulfide to give derivatives ( 6) and ( 9). Reaction of 7 under Gewald reaction condition afforded the thiophen-3-carbonitrile derivative (11) which consequently reacted with 4fluorobenzylidinemalononitrile, phenyl isothiocyanate to give compounds 12 and 15, respectively. The structures of these compounds were confirmed by infrared, mass and 1 H-NMR spectra. The measurement of potential cytotoxicity for the compound 11 was tested and has exhibit anticancer of liver and breast.