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

Synthesis of new medicinally important phenylsulphonyl aminoalkanamides and N-aryl p-toluene sulphonamides is reported. The reaction between benzenesulphonylchloride ۷ with valine gave ۳-methyl-۲-[phenylsulphonyl)amino]butanoic acid ۹ which is converted into ۲-[acetyl (phenylsulphonyl) amino]-۳-methyl butanoic acid ۱۰ by reaction with acetic anhydride in acetic acid. The reaction of the later with SOCl۲ and subsequently with NH۳ afforded ۲-[N-acetyl (phenylsulphonyl) amino]-۳-methyl butanamide intermediate ۱۱. The palladium catalysed reaction of the intermediate with readily available aryl chlorides and bromides afforded a variety of phenyl sulphonylaminoalkanamides ۱۳a-c. In another synthesis, p-toluenesulphonylchloride (۱۴) reacted with aqueous ammonia to give ۴-methyl benzenesulphonamide ۱۵ which is converted into N-(۴-hydroxylphenyl)-۴-methylbenzene sulphonamide ۱۷a, N-(۴-formyl phenyl)-۴-methyl benzene sulphonamide ۱۷b, N-(۴-aminophenyl)-۴-methyl benzenesulphonamide ۱۷c, ۴-methyl-N-(۲-methylphenyl) benzene sulphonamide ۱۷d, N-(۴-Methoxyphenyl)-۴-methyl benzenesulphonamide ۱۷e in good yields, by reaction with ۴-chlorophenol, ۴-bromobenzaldehyde , ۴-bromoaniline, ۲-chlorotoluene and ۱-bromo-۲-methoxybenzene, respectively. Structures of the synthesized compounds were confirmed by spectroscopic and elemental analytical data

کلیدواژه ها:

Sulphonamides ، Organosulfur ، Anticancer ، methotrexate ، Synthesis