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Synthesis 2021; 53(06): 1137-1148
DOI: 10.1055/s-0040-1706474
paper

Highly Functionalized Pyrrolylpyridines from 2-(Acylethynyl)-pyrroles

Denis N. Tomilin
,
Lyubov N. Sobenina
,
Igor A. Ushakov
,
Boris A. Trofimov∗
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033, Irkutsk, Russia   Email: boris_trofimov@irioch.irk.ru
› Author AffiliationsThis work was supported by the Russian Science Foundation (Project 19-73-10063).
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Abstract

A novel family of pharmaceutically prospective, densely functionalized (aryl-, hetaryl-, acyl-, and vinyl-substituted) pyrrolylpyridines has been assembled in up to 95% yields via the amination (NH4Cl/K2CO3/DMSO system, 90 °C, 16 h) of 2-(acylethynyl)pyrroles, followed by cyclization (MeOH, reflux, 6 h, up to 90% yield) of the formed intermediate 1-(pyrrol-2-yl)-1-aminoenones with acetylenic ketones (Bohlmann–Rahtz reaction). The intermediate pyrrolyl aminodienones, prospective building blocks for organic synthesis, can be separately synthesized (DMSO, 90 °C, 6 h) in 70–86% yields. A novel facet of this chemistry is stereoselective synthesis of C-vinylated pyridines, (E)-3-[5-acyl-2-aryl-6-(pyrrol-2-yl)pyridin-3-yl]-1-arylprop-2-en-1-ones, by involving the second molecule of acylacetylene into the reaction.

Key words

2-(acylethynyl)pyrroles - 1-(pyrrol-2-yl)-1-aminoenones - acetylenic ketones - aminodienones - intramolecular cyclization - pyrrolylpyridines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706474.
  • Supporting Information


Publication History

Received: 02 June 2020

Accepted after revision: 31 August 2020

Article published online:
05 October 2020

© 2020. Thieme. All rights reserved

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