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Розенцвейг, И. Б.; Levkovskaya, G. G.; Kondrashov, E. V.; Evstaf'eva, I. T.; Мирскова, А. Н.

doi:10.1023/a:1013899918370

Cited by 12 publications

(11 citation statements)

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“…The coupling constants J HH and J CF were determined with an accuracy of ±0. 1 Hz. Initial Schiff bases Ia [5], Ib, Ic [6], Id, Ie, and If [7] were synthesized by known methods. Pyrroles IIbIIf were prepared as described in [9].…”

Section: Methodsmentioning

confidence: 99%

“…The spectra contained two set of signals from aromatic and pyrrole rings. In addition, two sets of doublets typical of NH-CH fragment [1,5] were observed in the 1 H NMR spectra. Furthermore, the substitution pattern in the pyrrole ring was unambiguously proved by twodimensional 1 H-13 C HMBC technique optimized for n J CH = 10 Hz (coupling through 2-3 bonds).…”

Section: Ia-ifmentioning

confidence: 99%

“…Schiff bases Ia-If were synthesized according to the procedures developed previously from the corresponding N,N-dichloro sulfonamides and trichloroethylene or phenylacetylene [5][6][7]. Schiff bases Ia-Ic were brought into reactions with pyrroles without isolation from the reaction mixture; reactions of Schiff bases Id-If with pyrroles were carried out in carbon tetrachloride.…”

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confidence: 99%

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C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines

et al. 2009

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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.We previously reported [1] on the reactions of 4-chloro-N-(2,2,2-trichloroethylidene)benzenesulfonamide with pyrrole and 1-methyl-1H-pyrrole and synthesized the corresponding 2-[2,2,2-trichloro-1-(4-chlorophenylsulfonylamino)ethyl]pyrroles as C-amidoalkylation products. The reactions occurred both in the presence of BF 3 · Et 2 O as catalyst and in the absence of it; in the latter case, the process required a longer time. The yield of the alkylation product from unsubstituted pyrrole did not exceed 37% [1]. We recently found [2] that pyrrole reacts with N-(2,2,2-trichloroethylidene)-trifluoromethanesulfonamide to give both 2-mono-and 2,5-disubstituted products.With a view to reveal relations between the structure of Schiff bases, their reactivity, and direction of their reactions with hetarenes [3], we continued our studies on reactions of pyrrole derivatives with Schiff bases containing strong electron-withdrawing groups. In the present work we examined reactions of pyrrole and N-substituted pyrroles with N-(2,2,2-trichloroethylidene)-and N-(2,2-dichloro-2-phenylethylidene)-trifluoromethane-and -arenesulfonamides. The products of these reactions are characterized by unique combination of a pyrrole ring and aminosulfonyl and trichloromethyl groups which undoubtedly determine their ability to undergo further chemical transformations and significance as potential biologically active substances. We previously demonstrated that (2,2,2-trichloro-1-sulfonylaminoethyl)-substituted indoles can be converted into N-substituted indolylglycines, which may be regarded as biologically active heteroauxin derivatives modified with a sulfonylamino group [4]. Obviously, analogous processes may be typical of structurally related pyrrole derivatives.Thus development of procedures for the introduction of amino(polyhalo)ethyl substituents into a pyrrole ring could open convenient synthetic approaches to new functionalized pyrroles as precursors of N-sulfonyl-substituted pyrrolylaminoacetic acids, aminocarbonyl compounds, and heterocyclic systems. The importance of this problem is beyond doubt.Schiff bases Ia-If were synthesized according to the procedures developed previously from the corresponding N,N-dichloro sulfonamides and trichloroethylene or phenylacetylene [5][6][7]. Schiff bases Ia-Ic were brought into reactions with pyrroles without isolation from the reaction mixture; reactions of Schiff bases Id-If with pyrroles were carried out in carbon tetrachloride. Pyrroles IIb-IIf were prepared by...

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Section: Methodsmentioning

confidence: 99%

Section: Ia-ifmentioning

confidence: 99%

mentioning

confidence: 99%

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C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines

et al. 2009

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“…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.…”

Section: Introductionmentioning

confidence: 99%

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

Розенцвейг¹,

Rozentsveig²,

Levkovskaya³

et al. 2011

Arkivoc

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“…Schiff bases IIa-IIe were synthesized by reactions of N,N-dichloroarene-and trifluoromethanesulfonamides Ia-Ic with trichloroethylene, 1,2-dichloroethylene, or phenylacetylene as shown in Scheme 1 [3][4][5][6]. We examined reactions of a series of N-sulfonyl polychloro-acetaldehyde imines with indoles and some N-substituted indoles.…”

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confidence: 99%

10.1007/s11178-008-1010-2

2010

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N-(Polychloroethylidene)arene-and -trifluoromethanesulfonamides reacted with indole and N-substituted indoles to give the corresponding N-[2,2-dichloro(or 2,2,2-trichloro)-1-(1H-indol-3-yl)ethyl]-substituted sulfonamides. Unlike N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide, less electrophilic N-(polychloroethylidene)arenesulfonamides failed to react with 1-(4-nitrophenyl)-1H-indole. Previously unknown N,N′-bis(2,2-dichloroethylidene)biphenyl-4,4′-disulfonamide reacted with 1-benzyl-1H-indole at both azomethine fragments. Likewise, reactions of 1,6-bis(1H-indol-1-yl)hexane and 1,4-bis(1H-indol-1-ylmethyl)benzene with N-sulfonyl trichloroacetaldehyde imines involved both indole rings in the former.Previously unknown N,N′-bis(2,2-dichloroethylidene)biphenyl-4,4′-disulfonamide (IIf) was obtained from N, N,N′, [8] and 1,2-dichloroethylene (Scheme 2) by heating the reactants [molar ratio 1 : (20-30)] at the boiling REACTIONS OF N-(POLYCHLOROETHYLIDENE)ARENE-...

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Untitled

Cited by 12 publications

References 1 publication

C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines

C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines

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

10.1007/s11178-008-1010-2

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