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DOI: 10.1055/a-2295-8544
Synthesis of 4,5-Disubstituted Methyl 1H-Pyrrole-2-carboxylates from 3-Chloroacrylaldehydes and Hippuric Acid
This work was supported by the Russian Science Foundation (Grant No. 20-73-10043).
Abstract
The Vilsmeier–Haack reaction of ketones with DMF and POCl3 produced 3-chloroacrylcarbaldehydes, which were converted into the corresponding (Z)-4-[(Z)- or (Z)-4-[(E)-3-chloroallylidene)-2-phenyloxazol-5(4H)-ones] (azlactones) or their isomeric mixtures when heated with hippuric acid in propionic anhydride. It was shown that the alcoholysis products of these compounds, resulting from the opening of the oxazolone ring, undergo copper-catalyzed intramolecular cross-coupling reactions with the formation of methyl 1H-pyrrole-2-carboxylates. Thus, a one-pot method was developed for the synthesis of methyl 1H-pyrrole-2-carboxylates starting from 4-(3-chloroallylidene)-2-phenyloxazol-5(4H)-ones.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2295-8544.
- Supporting Information
Publikationsverlauf
Eingereicht: 03. Februar 2024
Angenommen nach Revision: 27. März 2024
Accepted Manuscript online:
27. März 2024
Artikel online veröffentlicht:
10. April 2024
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