UNEXPECTED FORMATION OF BENZOFURAN DERIVATIVES IN THE <i>C</i>-AMIDOALKYLATION OF <i>p</i>-CRESOL WITH 4-CHLORO-<i>N</i>-(2,2-DICHLORO-2-PHENYLETHYLIDENE)BENZENESULFONAMIDE

Authors

  • В. Ю. Серых A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • И. Б. Розенцвейг A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • Г. Н. Розенцвейг A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
  • К. А. Чернышев A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1342

Keywords:

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

Abstract

The C-amidoalkylation of p-cresol with 4-chloro-N-(2,2-dichloro-2-phenylethylidene)benzenesulfonamide 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.

Authors: V. Yu. Serykh, I. B. Rozentsveig, G. N. Rozentsveig, and K. A. Chernyshev.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (11), pp 1339-1344

http://link.springer.com/article/10.1007/s10593-012-0919-0

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Published

2013-12-11

Issue

No. 11 (2011)

Section

Original Papers