N-Functionally substituted imines of polychlorinated (brominated) aldehydes and ketones

Synthesis of N-arylsulfonylimidazolidine-4-ones from N-(2,2,2-trichloroethylidene)arenesulfonamides and monochloroacetamide

“…As expected, chloroacetamide shows lower reactivity in its reactions with chloral arenesulfonylimines than do the other amides of carboxylic acids which have been studied in similar processes. 4 This can be explained by the electron-accepting effect of the halogen atom.…”

“…The addition reactions of the amides of halocarboxylic acids with N-functionally substituted imines of polyhaloaldehydes should result in products which would be promising for the synthesis of heterocyclic compounds, but have not been studied yet, although the interaction of many amides with N-functionally substituted imines of polyhaloaldehydes have been studied in detail. 4 Investigation of the reactions of chloral arenesulfonylimines with monochloroacetamide seems to be important because it should give route for synthesizing new heterocyclic derivatives of N-arylsulfonyl-substituted imidazoles.…”

Unexpected reaction of N,N-dichloroarenesulfonamides with divinyl sulfide: formation of N-[2-chloro- and N-[2,2-dichloro-1-(arylsulfonylamino)ethyl]arenesulfonamides

“…1,1-Bis(amido)-2,2-dichloroethanes are known to be formed in reaction of N,N-dichloroamides 1 with 1,2-dichloroethylene. 14,42 It was assumed that the reaction proceeded via saturated N-chloro-adducts F followed by easy dechlorination resulting in N-sulfonyldichloroacetaldimines G. 13 Then arenesulfonamides are added to intermediate imines G (Scheme 3). Nucleophilic addition of arenesulfonamides to haloaldimines has been previously reviewed in detail.…”

“…A high reactivity of N,N-dichlorosulfonamides is caused by the ability of N-Cl group to enter into a homolytic or heterolytic cleavage depending on conditions to produce sulfonylamidyl radicals and atomic chlorine, sulfonylamidyl anions and cations of chlorine or nitrenes. N,N-Dichlorosulfonamides, in contrast to N,N-dichloroacylamides or N,Ndichlorourethanes are more stable under keeping but at the same time are more selective and reactive 14,23 in reactions because of strong electro-withdrawing nature of sulfonyl group and weak conjugation between SO2 group and nitrogen atom. Due to such features N,Ndichlorosulfonamides are useful for diverse chemical transformations.…”

“…Reaction of N,Ndichlorosulfonamides with alkenes is an efficient method for the synthesis of N-(-chloroalkyl)sulfonamides [9][10][11][12][13] and N-sulfonylpolyhaloaldimines [14][15][16][17][18][19] which were used as key reagents in further preparation of a large range of heterocyclic and open chained functionally substituted sulfonamide derivatives. 10,[14][15][16][17][18][19][24][25][26][27] In elemento-organic chemistry oxidative imination of heteroatomic compounds, and mainly sulfur containing reagents, are of great significance. 1,2,[20][21][22] Divinyl sulfide is an important representative of practically useful sulfur organic compounds.…”