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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 11, pp 1339–1344 | Cite as

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

  • V. Yu. Serykh
  • I. B. Rozentsveig
  • G. N. Rozentsveig
  • K. A. Chernyshev
Article

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.

Keywords

benzofurans p-cresol imines sulfonamides C-amidoalkylation acid catalysis heterocyclization nucleophilic addition 

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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • V. Yu. Serykh
    • 1
  • I. B. Rozentsveig
    • 1
  • G. N. Rozentsveig
    • 1
  • K. A. Chernyshev
    • 1
  1. 1.A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of SciencesIrkutskRussia

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