147116-69-6Relevant articles and documents
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.
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.
