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.