Synthesis of Some 2-sulphanilamido-1,4-Quinone Derivatives

Abstract

Ten new 2-sulfonilamido-1, 4-quinone derivatives were prepared in this work with their corresponding intermediates which include five p-aminobenzene sulphonilamido derivatives and two 1,4-quinone derivatives. Synthesis of the titled compounds was accomplished by chlorosulphonation of acetanilide and amination (sulfamethoxzole, 4-aminophenazone, sulfadoxine, sulphonilamide and sulfasulph onilamide) to furnish the p-acetamedobenzene sulphonilamido derivatives, the latter upon acid hydrolysis yielded p-amino benzene sulphonilamido derivatives. 1,4- quinone (1,4-naphthoquinone and 2-methyl-1,4-benzoquinoe were prepared by standard methods of chromic acid oxidation of naphthalene and o-crezol respectively. Coupling of the aminobenzene sulphonil amido derivative with 1,4- quinone moiety furnished the titled product. All synthesized compounds checked their reaction progress by (TLC) techniques. The structures of synthesized compounds were confirmed by some physical properties; (melting point) and spectroscopic analysis like (IR, 1H-NMR, 13C-NMR and MS).Synthetic designing and mechanisms of the reactions of the different groups of compounds were discussed.