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Unusually Facile Pyrrolization of 2-Acetylcoumarone Oxime with Acetylene

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    A. B. Zaitsev, E. Yu. Shmidt, A. M. Vasil’tsov, A. I. Mikhaleva, A. V. Afonin, I. A. Ushakov & D.-S. D. Toryashinova

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  1. A. B. Zaitsev
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  2. E. Yu. Shmidt
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  3. A. M. Vasil’tsov
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  4. A. I. Mikhaleva
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  5. A. V. Afonin
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  6. I. A. Ushakov
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  7. D.-S. D. Toryashinova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 524–529, April, 2005.

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Zaitsev, A.B., Shmidt, E.Y., Vasil’tsov, A.M. et al. Unusually Facile Pyrrolization of 2-Acetylcoumarone Oxime with Acetylene. Chem Heterocycl Compd 41, 444–448 (2005). https://doi.org/10.1007/s10593-005-0168-6

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  • DOI: https://doi.org/10.1007/s10593-005-0168-6

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