A novel regiospecific cascade synthesis of sulfonamide derivatives from N-(2-polychloroethyl)sulfonamides via chloroaziridine intermediates in the presence of mercaptoethanol

作者：Rozentsveig Igor B^*; Popov Aleksandr V; Rozentsveig Gulnur N; Serykh Valeriy Yu; Chernyshev Kirill A; Krivdin Leonid B; Levkovskaya Galina G

来源：Molecular Diversity, 2010, 14(3): 533-541.

DOI：10.1007/s11030-010-9231-z

• Sulfonamides
• Aziridines
• Imidoylchlorides
• Chloroimines
• 1,4-Oxathianes
• Ketones
• Cascade reactions

N-(1-Aryl-2-polychloroethyl)arenesulfonamides obtained on the basis of N,N-dichlorosulfoamides and polychloroethenes or phenylacetylene undergo a reaction cascade in the presence of mercaptoethanol. The reaction cascade opens a new route to the series of cyclic or open-chain sulfonamide derivatives. The process includes cyclization to aziridine intermediates, their further recyclization, and isomerization to imidoylchlorides or chloroimines, followed by substitution or reduction under the action of mercaptoethanol or hydrolysis. The final sulfonamide structures depend on the starting N-(polychloroethyl)sulfonamides. N-(2,2-Dichloroethyl)sulfonamides were transformed into sulfonamide-containing 1,4-oxathians while N-(2,2,2-trichloroethyl)sulfonamides were converted to N-(2-arylacetyl)arenesulfonamides. N-(2-Phenyl-2,2-dichloroethyl)sulfonamides form enamide derivatives that were transformed into aromatic ketones.

• 出版日期2010-8