Synthesis of 4,5-Disubstituted Methyl 1H-Pyrrole-2-carboxylates from 3-Chloroacrylaldehydes and Hippuric Acid

Anna L. Samsonenko; Anastasia S. Kostyuchenko; Tatyana Yu. Zheleznova; Vladislav Yu. Shuvalov; Evgenii B. Uliankin; Anton L. Shatsauskas; Alexander S. Fisyuk

doi:10.1055/a-2295-8544

Synthesis, Table of Contents

Synthesis 2024; 56(15): 2423-2431
DOI: 10.1055/a-2295-8544

paper

Synthesis of 4,5-Disubstituted Methyl 1H-Pyrrole-2-carboxylates from 3-Chloroacrylaldehydes and Hippuric Acid

Anna L. Samsonenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Anastasia S. Kostyuchenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Tatyana Yu. Zheleznova

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Vladislav Yu. Shuvalov

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Evgenii B. Uliankin

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Anton L. Shatsauskas

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Alexander S. Fisyuk ∗

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

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Abstract

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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

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References

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