UNUSUALLY FACILE PYRROLIZATION OF 2-ACETYLCOUMARONE OXIME WITH ACETYLENE

Authors

  • А. Б. Зайцев Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • E. Ю. Шмидт Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • A. M. Васильцов Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • A. И. Михалева Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • А. В. Афонин Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • И. А. Ушаков Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • Д.-С. Д. Торяшинова Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033

DOI:

https://doi.org/10.1007/8319

Keywords:

acetylene, O-vinyl oxime, 1-vinylpyrrole, 2-acetylcoumarone oxime, pyrrole

Abstract

The oxime of 2-acetylcoumarone reacts with  acetylene under pressure in the system KOH–DMSO unusually readily forming 2-(2-pyrrolyl)coumarone and the corresponding O-vinyl oxime. Under more rigid conditions 2-(1-vinyl-2-pyrrolyl)coumarone is formed. The possibility of a two-stage transformation of 2-acylcoumarones into 2-pyrrolylcoumarones has therefore been demonstrated for the first time.

How to Cite
Zaitsev, A. B.; Shmidt, E. Yu.; Vasil'tsov, A. M.; Mikhaleva, A. I.; Afonin, A. V.; Ushakov, I. A.; Toryashinova, D.-S. D.  Chem. Heterocycl. Compd. 2005, 41, 444. [Khim. Geterotsikl. Soedin. 2005, 524.]

For this article in the English edition, see DOI 10.1007/s10593-005-0168-6


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Published

2023-11-16

Issue

No. 4 (2005)

Section

Original Papers