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Synthesis
DOI: 10.1055/a-2295-8544
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Synthesis of 4,5-Disubstituted Methyl 1H-Pyrrole-2-carboxylates from 3-Chloroacrylaldehydes and Hippuric Acid

Anna L. Samsonenko
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Anastasia S. Kostyuchenko
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Tatyana Yu. Zheleznova
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Vladislav Yu. Shuvalov 
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Evgenii B. Uliankin
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Anton L. Shatsauskas
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Alexander S. Fisyuk  ∗
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
› Author AffiliationsThis work was supported by the Russian Science Foundation (Grant No. 20-73-10043).
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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.

Key words

conjugation - cyclization - heterocycles - pyrroles - catalysis - copper

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2295-8544.
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Publication History

Received: 03 February 2024

Accepted after revision: 27 March 2024

Accepted Manuscript online:
27 March 2024

Article published online:
10 April 2024

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