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Rearrangement of 3-ethoxycarbonyl-5-hydroxyimino-2-methyl-4-oxonaphtho[1,2-b]furan and 3-ethoxycarbonyl-5-hydroxyimino-2-methyl-4-oxo-1-phenylbenzo[g]indole by the action of benzenesulfonyl chloride in an alkaline medium

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The treatment of 3-ethoxycarbonyl-2-methyl-4,5-dioxonaphtho[1,2-b]furan 5-monoximes and also the similarly substituted benzo[g]indole with benzenesulfonyl chloride in an alkaline medium give 5-(2-cyanophenyl)-3-ethoxycarbonyl-2-methylfuran-4-carboxylic and pyrrole-4-carboxylic acids with high yields as a result of a second-order Beckmann rearrangement. The structures of the initial and final compounds were confirmed by analysis of their mass spectra.

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Authors
  1. A. P. Stankyavichus
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  2. L. M. M. Stankyavichene
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  3. P. B. Terent'ev
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Additional information

Institute of Cardiology, Kaunas Medical Academy, Kaunas 233007, Lithuania M. V. Lomonosov Moscow State University, Moscow 119899, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1462-1465, November, 1999.

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Stankyavichus, A.P., Stankyavichene, L.M.M. & Terent'ev, P.B. Rearrangement of 3-ethoxycarbonyl-5-hydroxyimino-2-methyl-4-oxonaphtho[1,2-b]furan and 3-ethoxycarbonyl-5-hydroxyimino-2-methyl-4-oxo-1-phenylbenzo[g]indole by the action of benzenesulfonyl chloride in an alkaline medium. Chem Heterocycl Compd 35, 1272–1275 (1999). https://doi.org/10.1007/BF02251993

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  • DOI: https://doi.org/10.1007/BF02251993

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