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Unexpected formation of benzofuran derivatives in the C-amidoalkylation of p-cresol with 4-chloro-N-(2,2-dichloro-2-phenylethylidene)benzenesulfonamide*

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Chemistry of Heterocyclic Compounds Aims and scope

The C-amidoalkylation of p-cresol with 4-chloro-N-(2,2-dichloro-2-phenylethylidene)benzenesulfon-amide in the presence of H2SO4, oleum, or a mixture of H2SO4 and P4O10 was studied for the first time. It was shown that the reaction not only leads to the targeted 4-chloro-N-[2,2-dichloro-1-(2-hydroxy-5-methylphenyl)-2-phenylethyl]benzenesulfonamide but is also accompanied by unexpected formation of the heterocyclic derivatives 4-chloro-N-(5-methyl-2-phenyl-1-benzofuran-3-yl)benzenesulfonamide and 5-methyl-3-phenyl-2-benzofuran-2(3H)-one.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky St., Irkutsk, 664033, Russia

    V. Yu. Serykh, I. B. Rozentsveig, G. N. Rozentsveig & K. A. Chernyshev

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  1. V. Yu. Serykh
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  2. I. B. Rozentsveig
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  3. G. N. Rozentsveig
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  4. K. A. Chernyshev
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Correspondence to I. B. Rozentsveig.

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*Dedicated to Academician M. G. Voronkov on his 90th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1617-1622, November, 2011.

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Serykh, V.Y., Rozentsveig, I.B., Rozentsveig, G.N. et al. Unexpected formation of benzofuran derivatives in the C-amidoalkylation of p-cresol with 4-chloro-N-(2,2-dichloro-2-phenylethylidene)benzenesulfonamide*. Chem Heterocycl Comp 47, 1339–1344 (2012). https://doi.org/10.1007/s10593-012-0919-0

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  • DOI: https://doi.org/10.1007/s10593-012-0919-0

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