Synthesis of Medicinally Relevant Phenyl Sulphonylamino Alkanamides and Naryl Ptoluenesulphonamides

Synthesis of new medicinally important phenylsulphonyl aminoalkanamides and N-aryl ptoluene sulphonamides is reported. The reaction between benzenesulphonylchloride 7 and valine gave 3-methyl-2-[phenylsulphonyl)amino]butanoic acid 9 which was converted into 2- [acetyl (phenylsulphonyl) amino]-3-methyl butanoic acid 10 by reacting with acetic anhydride in acetic acid. The reaction of the latter with SOCl2 and the former with NH3 afforded 2-[Nacetyl (phenylsulphonyl) amino]-3-methyl butanamide intermediate 11. The palladiumcatalyzed reaction of the intermediate with readily available aryl chlorides and bromides afforded a variety of phenyl sulphonylaminoalkanamides 13a-c. In another synthesis, ptoluenesulphonylchloride (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.