Configurational assignment of <i>N</i>‐arylsulfonylimines of α‐polychloroaldehydes

Krivdin, Leonid B.; Chernyshev, K. A.; Rosentsveig, G. N.; Ushakova, I. V.; Rosentsveig, I. B.; Levkovskaya, G. G.

doi:10.1002/mrc.2070

Cited by 16 publications

(10 citation statements)

References 18 publications

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“…The 1 H and 13 C NMR spectra of compounds 4a and 4b were in agreement with the proposed structures. The resonances due to the NH-CH-NH fragment, the double doublet at 6.46-6.48 ppm, corresponding to the CH group, as well as two doublets at 8.17-8.24 and 8.93-8.95 ppm, corresponding to NH groups with a coupling constant of 9.5-9.8 Hz, are symptomatic for these adducts.…”

Section: Methodssupporting

confidence: 66%

“…Compound 3a was synthesized according to the previously developed method. 30 1 H, 13 С NMR spectra were recorded on a Bruker DPX-400 spectrometer (400.61, 100.13 MHz, respectively) with TMS as an internal standard. IR spectra were recorded on a Bruker IFS-25 instrument on KBr discs.…”

Section: Methodsmentioning

confidence: 99%

“…8,[10][11][12] N-Sulfonyl-substituted phenyldichloroacetaldimines of the type 1 are key representatives of activated electrophilic imines, that are available through previously developed methods based on free-radical reaction of N,N-dichlorosulfonamides with phenylacetylene (Scheme 1). 13,14 Until now, no alternative syntheses to N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides of type 1 have been developed. Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

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One-pot regioselective synthesis of new 5-(arylsulfonylamino)imidazo[2,1-b]thiazoles

Serykh¹,

Chernysheva²,

Kondrashov³

et al. 2015

Arkivoc

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Section: Methodssupporting

confidence: 66%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

One-pot regioselective synthesis of new 5-(arylsulfonylamino)imidazo[2,1-b]thiazoles

Serykh¹,

Chernysheva²,

Kondrashov³

et al. 2015

Arkivoc

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show abstract

“…[224][225][226][227]. For instance, in a study of iminodihydrofurans, calculated spin-spin coupling constants were compared with experimental data to establish the configuration of the C@NH group (orientation of the nitrogen lone pair) and the conformation of the O@CAC@C fragment (s-cis vs. s-trans) [226].…”

Section: Configurational and Conformational Analysismentioning

confidence: 99%

The quantum-chemical calculation of NMR indirect spin–spin coupling constants

Helgaker

Jaszuński

Pecul

2008

Progress in Nuclear Magnetic Resonance Spectroscopy

265

256

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“…Initial N-sulfonyl imines I and II are readily available via previously developed procedure which is based on radical addition of trichloroethylene and phenylacetylene to N,N-dichloroarenesulfonamides [1,17,18]. In reactions with imines I and II dithiooxamide acts as nitrogen-centered nucleophile which adds at the activated C=N bond.…”

mentioning

confidence: 99%

Functionalization of highly electrophilic N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene) arenesulfonamides with dithiooxamide

et al. 2012

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Depending on the reactant ratio, dithiooxamide (ethanedithioamide) reacted as N-nucleophile or N,N′-binucleophile with highly electrophilic aldimines, N-(2,2,2-trichloroethylidene)-and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides, to give the corresponding mono-or bis-adducts, N-[2-polychloro-1-(arylsulfonylamino)ethyl]ethanedithioamides or N,N′-bis[2-polychloro-1-(arylsulfonylamino)ethyl]ethanedithioamides, in good yield. I, III, V, X = Cl; II, IV, VI, X = Ph; Ar = Ph (a), 4-MeC 6 H 4 (b), 4-ClC 6 H 4 (c).Reactions of highly electrophilic N-sulfonyl polychloroaldehyde imines with oxygen-, nitrogen-, sulfur-, and carbon-centered nucleophiles underlie preparatively efficient approaches to a broad series of N-polyhaloalkyl sulfonamides. The latter possess various functional groups, including reactive NH group and polyhalomethyl fragments, and are used in the synthesis of difficultly accessible acyclic and heterocyclic sulfonamides [1][2][3][4][5][6][7]. We previously showed [8] that addition of thioamides to N-(polychloroethylidene)-arenesulfonamides leads to the formation of polyfunctional adducts capable of undergoing cyclization to difficultly accessible 4-sulfonylaminothiazoles [6,7]. In continuation of these studies, in the present work we examined reactions of N-(2,2,2-trichloroethylidene)-and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides I and II with dithiooxamide with a view to develop methods for the preparation of functionalized N-haloalkyl amides as substrates for subsequent heterocyclization and biological screening.Dithiooxamide derivatives attract interest as starting compounds for the synthesis of a number of S,Nheterocycles [9,10]. In addition, dithiooxamide and its derivatives are used as ligands to obtain metal complexes [11][12][13] and catalysts in asymmetric syntheses [11], as well as in the preparation of inorganic nanotubes [13]. Structural studies on dithiooxamide and its derivatives performed by spectral and quantumchemical methods [14][15][16] are important from the theoretical viewpoint.

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Configurational assignment of N‐arylsulfonylimines of α‐polychloroaldehydes

Cited by 16 publications

References 18 publications

One-pot regioselective synthesis of new 5-(arylsulfonylamino)imidazo[2,1-b]thiazoles

One-pot regioselective synthesis of new 5-(arylsulfonylamino)imidazo[2,1-b]thiazoles

The quantum-chemical calculation of NMR indirect spin–spin coupling constants

Functionalization of highly electrophilic N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene) arenesulfonamides with dithiooxamide

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