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DOI: 10.1055/s-0040-1706474
Highly Functionalized Pyrrolylpyridines from 2-(Acylethynyl)-pyrroles
This work was supported by the Russian Science Foundation (Project 19-73-10063).
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 - pyrrolylpyridinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706474.
- Supporting Information
Publikationsverlauf
Eingereicht: 02. Juni 2020
Angenommen nach Revision: 31. August 2020
Artikel online veröffentlicht:
05. Oktober 2020
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