Benzene, toluene, and 2-chlorothiophene regioselectively react with N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides in the presence of oleum to give N-[1-aryl(or hetaryl)-2,2-dichloro-2-phenylethyl]arenesulfonamides. Analogous C-amidoalkylation products are formed by the action of N-(2,2-dichloro-1-hydroxy-2-phenylethyl)- and N-(1-arylsulfonylamino-2,2-dichloro-2-phenylethyl)arenesulfonamides on toluene and 2-chlorothiophene in concentrated sulfuric acid.
Amidine derivatives of α-arylglycines from N-(1-aryl-2,2,2-trichloroethyl)amides of arenesulfonic acids and secondary amines
作者:Igor B. Rozentsveig、Galina G. Levkovskaya、Gulnur N. Rozentsveig、Anna N. Mirskova、Leonid B. Krivdin、Ludmila I. Larina、Aleksandr I. Albanov
DOI:10.1016/j.tetlet.2005.10.079
日期:2005.12
The interaction of N-(1-aryl-2,2,2-trichloroethyl)amides of arenesulfonic acids with secondary amines or their salts in the presence of inorganic bases involves the formation of chloroaziridine intermediates. Depending upon the solvent and reagent ratio, the reaction results in N-[1-dialkylamino-2-chloro-2-arylethylidene]-, N-[2-dialkylamino-1-chloro-2-arylethylidene]-, N-[1,2-bis(dialkylamino)-2-arylethylidene]-