Synthesis of Medicinally Relevant Phenyl Sulphonylamino Alkanamides and N-aryl P-toluenesulphonamides

Abstract

Synthesis of new medicinally important phenylsulphonyl aminoalkanamides and N-aryl p-toluene sulphonamides is reported. The reaction between benzenesulphonylchloride 7 with valine gave 3-methyl-2-[phenylsulphonyl)amino]butanoic acid 9 which is converted into 2-[acetyl (phenylsulphonyl) amino]-3-methyl butanoic acid 10 by reaction with acetic anhydride in acetic acid. The reaction of the later with SOCl2 and subsequently with NH3 afforded 2-[N-acetyl (phenylsulphonyl) amino]-3-methyl butanamide intermediate 11. The palladium catalysed reaction of the intermediate with readily available aryl chlorides and bromides afforded a variety of phenyl sulphonylaminoalkanamides 13a-c. In another synthesis, p-toluenesulphonylchloride (14) reacted with aqueous ammonia to give 4-methyl benzenesulphonamide 15 which is converted into N-(4-hydroxylphenyl)-4-methylbenzene sulphonamide 17a, N-(4-formyl phenyl)-4-methyl benzene sulphonamide 17b, N-(4-aminophenyl)-4-methyl benzenesulphonamide 17c, 4-methyl-N-(2-methylphenyl) benzene sulphonamide 17d, N-(4-Methoxyphenyl)-4-methyl benzenesulphonamide 17e in good yields, by reaction with 4-chlorophenol, 4-bromobenzaldehyde , 4-bromoaniline, 2-chlorotoluene and 1-bromo-2-methoxybenzene, respectively. Structures of the synthesized compounds were confirmed by spectroscopic and elemental analytical data