Chemistry of Heterocyclic Compounds

, Volume 35, Issue 11, pp 1272–1275 | Cite as

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

  • A. P. Stankyavichus
  • L. M. M. Stankyavichene
  • P. B. Terent'ev


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.


Chloride Mass Spectrum Organic Chemistry Indole Furan 
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  1. 1.
    A. N. Kost and A. P. Stankyavichus,Zh. Org. Khim.,6, 1022 (1970).Google Scholar
  2. 2.
    P. B. Terent'ev, L. Mazhilis, A. G. Kalandarishvili, and A. P. Stankyavichus,Khim. Geterotsikl. Soedin., No. 8, 1052 (1986).Google Scholar
  3. 3.
    A. P. Stankyavichus, P. B. Terent'ev, and O. A. Solov'ev,Khim. Geterotsikl. Soedin., No. 9, 1243 (1989).Google Scholar
  4. 4.
    A. N. Kost, A. P. Stankyavichus, L. N. Zhukauskaite, and I. M. Shulyakene,Khim. Geterotsikl. Soedin., No. 4, 509 (1971).Google Scholar
  5. 5.
    A. N. Grinev, Hun Shii Tsun, and A. P. Terent'ev,Zh. Obshch. Khim.,32, 1951 (1962).Google Scholar
  6. 6.
    P. B. Terent'ev and A. P. Stankyavichus,Mass Spectrometry of Biologically Active Nitrogen Compounds [Russian translation], Mokslas, Vilnius (1987).Google Scholar
  7. 7.
    H. Budzikiewicz, C. Djerassi, and D. Williams,Mass Spectrometry of Organic Compounds, Holden-Day, San Francisco, London, Cambridge, Amsterdam (1967), p. 605.Google Scholar
  8. 8.
    A. N. Grinev, Hun Shii Tsun, and A. P. Terent'ev,Zh. Obshch. Khim.,30, 3668 (1960).Google Scholar

Copyright information

© KluwerAcademic/Plenum Publishers 1999

Authors and Affiliations

  • A. P. Stankyavichus
  • L. M. M. Stankyavichene
  • P. B. Terent'ev

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