1107692-82-9Relevant academic research and scientific papers
C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines
Kondrashov,Rudyakova,Rozentsveig,Rozentsveig,Chernyshev,Krivdin,Levkovskaya
experimental part, p. 1365 - 1374 (2010/01/11)
N-(Trifluoromethylsulfonyl) and N-arylsulfonyl polychloroacetaldehyde imines reacted with pyrrole, 1-alkyl-, 1-benzyl-, and 1-(4-nitrophenyl)- substituted pyrroles, and bis-pyrroles to give the corresponding 2-[1-(sulfonylamino)polychloroethyl]-1H-pyrroles or mixtures of 2- and 3-[1-(sulfonylamino)polychloroethyl]-1H-pyrroles, depending on the nature of the Schiff base and substituent on the pyrrole nitrogen atom and reaction conditions. The first synthesis of 2,5-disubstituted NH-pyrrole by reaction of pyrrole with Schiff bases was described.
Regioselectivity in the reactions of N-(polychloroethylidene)-sulfonamides with 1H-pyrrole and 1-methyl-1H-pyrrole
Rozentsveig,Shainyan,Kondrashov,Rudyakova,Rozentsveig,Chernyshev,Levkovskaya
experimental part, p. 1332 - 1337 (2009/07/17)
N-(2,2,2-Trichloroethylidene)arenesulfonamides react with 1H-pyrrole and 1-methyl-1H-pyrrole to give the corresponding N-[2,2,2-trichloro-1-(1H-pyrrol-2- yl)ethyl]arenesulfonamides. The reaction of N-(2,2,2-trichloroethylidene) trifluoromethanesulfonamide with pyrrole leads to a mixture of 2-mono-and 2,5-disubstituted pyrroles, whereas in the reaction with 1-methyl-1H-pyrrole only the 2-substituted compound is formed. N-(2,2-Dichloro-2-phenylethylidene)- 4-methylbenzenesulfonamide reacts with 1H-pyrrole to form N-[2,2-dichloro-2- phenyl-1-(1H-pyrrol-2-yl)ethyl]-4-methylbenzenesulfonamide, and its reaction with 1-methyl-1H-pyrrole gives a mixture of 2-and 3-monosubstituted derivatives. The results of quantum-chemical calculations of the initial reactants and products indicate that the process is orbital-controlled. A good agreement is observed between the experimental data and theoretical conclusions concerning the dependence of the reaction regioselectivity on the nature of substituents in the electrophile molecule.
