REGIO- AND DIASTEREOSELECTIVE SYNTHESIS OF <i>N</i>-SUBSTITUTED 2-ACYL-3-ARYL-3,5-DIHYDROFURO[3,2-<i>c</i>]PYRIDIN-4(2<i>H</i>)-ONES

Authors

  • Евгений А. Кветкин Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Дмитрий В. Осипов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Павел Е. Красников Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Виталий А. Осянин Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Юрий Н. Климочкин Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

DOI:

https://doi.org/10.1007/5898

Keywords:

2-acyl-3-aryl-3, 5-dihydrofuro[3, 2-c]pyridin-4(2H)-ones, pyridinium ylides, MIRC reaction, multicomponent reactions.

Abstract

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(2H)-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.

Author Biographies

Дмитрий В. Осипов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

к.х.н., доцент кафедры органической химии

Павел Е. Красников, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

старший научный сотрудник

Виталий А. Осянин, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

д.х.н., профессор кафедры органической химии

Юрий Н. Климочкин, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

д.х.н., профессор, заведующий кафедрой органической химии

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Published

2020-11-26

Issue

Vol. 56 No. 11 (2020)

Section

Original Papers