Regio- and diastereoselective synthesis of N-substituted 2-acyl-3-aryl-3,5-dihydrofuro[3,2-c]pyridin-4(2H)-ones

Regio- and diastereoselective synthesis of N-substituted 2-acyl-3-aryl-3,5-dihydrofuro[3,2-c]pyridin-4(2H)-ones

The three-component condensation of pyridinium acylmethylides generated in situ with aromatic aldehydes and 4-hydroxy-6-methylpyridones gave a series of 2-acyl-3-aryl-3,5-dihydrofuro[3,2- c ]pyridin-4(2 H )-ones. The reaction proceeds diastereoselectively with the formation of trans -isomers and rep...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-11, Vol.56 (11), p.1423-1428
Hauptverfasser: Kvetkin, Evgeny А., Osipov, Dmitry V., Krasnikov, Pavel E., Osyanin, Vitaly А., Klimochkin, Yuri N.
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Zusammenfassung:The three-component condensation of pyridinium acylmethylides generated in situ with aromatic aldehydes and 4-hydroxy-6-methylpyridones gave a series of 2-acyl-3-aryl-3,5-dihydrofuro[3,2- c ]pyridin-4(2 H )-ones. The reaction proceeds diastereoselectively with the formation of trans -isomers and represents a cascade process involving the Knoevenagel condensation, the carbo-Michael reaction, and intramolecular nucleophilic substitution.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02832-z