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

Autor: Samsonenko, Anna L., Kostyuchenko, Anastasia S., Zheleznova, Tatyana Yu., Shuvalov, Vladislav Yu., Uliankin, Evgenii B., Shatsauskas, Anton L., Fisyuk, Alexander S.
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Zdroj: Synthesis; Aug2024, Vol. 56 Issue 15, p2423-2431, 9p
Abstrakt: 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(4 H)-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 1 H -pyrrole-2-carboxylates. Thus, a one-pot method was developed for the synthesis of methyl 1 H -pyrrole-2-carboxylates starting from 4-(3-chloroallylidene)-2-phenyloxazol-5(4 H)-ones. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index