147116-69-6Relevant academic research and scientific papers
Two-Step Regioselective Synthesis of 3-(Sulfonylamino)imidazo[1,2-a]pyrimidines from 2-Aminopyrimidines and N-(2,2-Dichloro-2-phenylethylidene)arensulfonamides
Rozentsveig, Igor B.,Serykh, Valery Yu.,Chernysheva, Gulnur N.,Kondrashov, Evgeniy V.,Fedotova, Alena I.,Ushakov, Igor A.,Tretyakov, Evgeny V.,Romanenko, Galina V.
, p. 6547 - 6557 (2016/02/18)
The reaction of 2-aminopyrimidines with N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides affords the corresponding products of nucleophilic addition to the azomethine group, N-[2,2-dichloro-2-phenyl-1-(heterylamino)ethyl]sulfonamides, in good yields.
A new synthesis of 3-(sulfonamido)benzofurans through an acid-promoted cascade reaction of N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides with para-substituted phenols
Rozentsveig, Igor B.,Rozentsveig, Gulnur N.,Serykh, Valeriy Yu.,Chernyshev, Kirill A.,Levkovskaya, Galina G.
scheme or table, p. 4415 - 4421 (2011/10/04)
2-Phenyl-3-(sulfonamido)benzofurans are produced in a cascade reaction of N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides with para-substituted phenols in the presence of the superacid H2SO4/P 4O10 system. A convenient synthetic approach to 2-aryl-3-(sulfonamido)benzofurans through a cascade reaction of available N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides withpara-substituted phenols in the presence of the superacid H2SO4/P 4O10 system was developed.
N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides in reactions with secondary amines
Rozentsveig,Rozentsveig,Mirskova,Chernyshev,Krivdin,Levkovskaya
experimental part, p. 1371 - 1379 (2009/02/07)
N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides were synthesized by a modified procedure, and their reactions with secondary amines were studied for the first time. Reactions of imines with dialkylamines proceed at room temperature to afford α,α-dichloromethylbenzene and N,N-dialkyl-N′-(arenesulfonyl)formamidines arising from the haloform cleavage of the initially formed unstable N-(1-dialkylamino-2,2-dichloro-2- phenylethyl)arenesulfonamides. When the reaction is carried out upon cooling to 0°C, the products of the nucleophilic addition of secondary amines to azomethines, N-(1-dialkylamino-2,2-dichloro-2-phenylethyl) are formed in yields of no higher than 5%. Nonempirical calculations of 13C-1H spin-spin coupling constants and their experimental measurements for the series of the synthesized N-arenesulfonamides were performed to show that these compounds exist in solutions exclusively as E isomers. Preferable conformations of the investigated compounds and the relative energies of their E and Z isomers in the gas phase were determined by quantum-chemical calculations at the MP2/6-311G**level of theory. The NMR spectral data revealed restricted rotation of the N,N-dialkylamino group about the partially double C-NAlk2 bond in the molecules of N-arenesulfonylformamidines.
SYNTHESIS OF n-(2,2-DIHALOGENO-2-PHENYLETHYLIDENE)BENZENESULFONAMIDE FROM N,N-DIHALOGENOBENZENESULFONAMIDE AND PHENYLACETYLENE
Drozdova, T. I.,Levkovskaya, G. G.,Mirskova, A. N.
, p. 968 - 972 (2007/10/02)
The reaction of N,N-dichloro- and N,N-dibromobenzenesulfonamides with phenylacetylene leads to benzenesulfonyliminodichlorophenylacetaldehyde.The latter enters into nucleophilic addition with water, ethanol, benzoic and acetic acids, and amides at the azomethine bond, and N-(2,2-dichloro-2-phenyl-1-R-ethyl)benzenesulfonamides are obtained.
