Synthesis 2022; 54(04): 1134-1144
DOI: 10.1055/a-1681-4164
paper

Functionalized Bipyrroles and Pyrrolyl-Aminopyrones from Acylethynylpyrroles and Diethyl Aminomalonate

Authors

  • Maxim D. Gotsko

    a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
  • Ivan V. Saliy

    a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
  • Lyubov N. Sobenina

    a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
  • Igor A. Ushakov

    a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
  • Victoriya V. Kireeva

    b   Biomedical Research and Technology Department of the Irkutsk Scientific Center of the Russian Academy of Sciences, 283 Lermontov Str., 664033 Irkutsk, Russian Federation
  • Boris A. Trofimov

    a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation

This work was supported by the Russian Science Foundation (grant no. 19-73-10063).


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Abstract

An efficient method for the synthesis of 1H,1′H-2,3′-bi­pyrroles (up to 72% yield) by the cyclocondensation of easily available 2-(acylethynyl)pyrroles with diethyl aminomalonate hydrochloride has been developed. The reaction proceeds under reflux in MeCN (6 h) in the presence of Cs2CO3. Under the same conditions, 2-(acylethynyl)pyrroles with bulky (benzyl and octyl) substituents at nitrogen atom react with diethyl aminomalonate to afford 1H,2′H-2,3′-bipyrroles and pyrrolyl-aminopyrones.

Supporting Information



Publication History

Received: 05 October 2021

Accepted: 28 October 2021

Accepted Manuscript online:
28 October 2021

Article published online:
14 December 2021

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