ChemInform Abstract: Synthesis of 1,3‐Oxazolidin‐4‐ones and 1,3‐Thiazolidin‐4‐ones from ( Trichloroethylidene)arenesulfonamides.

Evstaf'eva, I. T.; Levkovskaya, G. G.; Bannikova, O. B.; Мирскова, А. Н.

doi:10.1002/chin.199418137

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“…Such transformations provide convenient approaches to various functionalized sulfonamide derivatives [1][2][3][4][5][6][7][8][9][10][11][12][13][14] as interesting models for stereochemical studies [5-8] and reagents [1,[9][10][11][12][13][14][15][16].…”

Section: Short Communicationsmentioning

confidence: 99%

Section: Short Communicationsmentioning

confidence: 99%

“…Furthermore, addition of alkanethiols [1, 13], 2-sulfanylethanol [14], and 2-sulfanylacetic acid [15,16] to the activated C=N bond in N-(trichloroethylidene)arenesulfonamides was studied. Polyfunctional S-adducts obtained in these reactions were then used to synthesize thiazolidine derivatives [12][13][14][15][16].Reactions of N-(trichloroethylidene)arenesulfonamides (that are readily obtained in one step from accessible N,N-dichloroarenesulfonamides and trichloroethylene [1]) with aromatic or heteroaromatic thiols were not reported previously. On the other hand, expected products of such reactions may be promising for the development of procedures for the preparation of fused heterocyclic systems, as well as of N-protected hetarylsulfanyl-substituted amino acids.…”

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confidence: 99%

“…However, only a few examples of analogous reactions with sulfur-centered nucleophiles were reported; in particular, addition of phenylmethanethiol, benzenethiols, 2-sulfanylethanol, and 2-sulfanylacetic acid to N-[1-(dialkoxyphosphoryl)-2,2,2-trichloroethylidene]-arenesulfonamides was described in [12]. Furthermore, addition of alkanethiols [1,13], 2-sulfanylethanol [14], and 2-sulfanylacetic acid [15,16] to the activated C=N bond in N-(trichloroethylidene)arenesulfonamides was studied. Polyfunctional S-adducts obtained in these reactions were then used to synthesize thiazolidine derivatives [12][13][14][15][16].…”

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confidence: 99%

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Synthesis of N-[1-(1H-Benzimidazol-2-ylsulfanyl)-2,2,2-trichloroethyl]arenesulfonamides by Reaction of N-(2,2,2-Trichloroethylidene)arenesulfonamides with 1H-benzimidazole-2-thiol

2012

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SHORT COMMUNICATIONSElectron-deficient character of the azomethine moiety in N-sulfonyl imines derived from polyhalocarbonyl compounds is determined by the effect of strong electron-withdrawing substituents, which favors their reactions with various nucleophiles and polynucleophiles [1]. Such transformations provide convenient approaches to various functionalized sulfonamide derivatives [1][2][3][4][5][6][7][8][9][10][11][12][13][14] as interesting models for stereochemical studies [5-8] and reagents [1,[9][10][11][12][13][14][15][16].Reactions of N-sulfonyl polyhaloaldehyde and polyhaloketone imines with oxygen-and nitrogencentered nucleophiles have been studied in most detail. However, only a few examples of analogous reactions with sulfur-centered nucleophiles were reported; in particular, addition of phenylmethanethiol, benzenethiols, 2-sulfanylethanol, and 2-sulfanylacetic acid to N-[1-(dialkoxyphosphoryl)-2,2,2-trichloroethylidene]-arenesulfonamides was described in [12]. Furthermore, addition of alkanethiols [1, 13], 2-sulfanylethanol [14], and 2-sulfanylacetic acid [15,16] to the activated C=N bond in N-(trichloroethylidene)arenesulfonamides was studied. Polyfunctional S-adducts obtained in these reactions were then used to synthesize thiazolidine derivatives [12][13][14][15][16].Reactions of N-(trichloroethylidene)arenesulfonamides (that are readily obtained in one step from accessible N,N-dichloroarenesulfonamides and trichloroethylene [1]) with aromatic or heteroaromatic thiols were not reported previously. On the other hand, expected products of such reactions may be promising for the development of procedures for the preparation of fused heterocyclic systems, as well as of N-protected hetarylsulfanyl-substituted amino acids.In continuation of our studies on reactions of sulfurcentered nucleophiles with N-sulfonyl imines derived from polyhalocarbonyl compounds the present communication reports on the reaction of N-(2,2,2-trichloroethylidene)arensulfonamides Ia and Ib with 1H-benzimidazole-2-thiol as a possible route to functionalized imidazole and sulfonamide derivatives. Ar = 4-ClC 6 H 4 (a), 4-MeC 6 H 4 (b).

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