THREE-COMPONENT SYNTHESIS OF 2-ACYL-2,3-DIHYDRO-4<i>H</i>-THIOCHROMENO[4,3-<i>b</i>]FURAN-4-ONES AND THEIR REDUCTIVE REARRANGEMENT INTO 4<i>H</i>,5<i>H</i>-THIOCHROMENO[4,3-<i>b</i>]PYRAN-5-ONES

Authors

  • Максим Р. Демидов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Анастасия Н. Доброквашина Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Дмитрий В. Осипов 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/10.1007/6105

Keywords:

2-acyl-2, 3-dihydro-4H-thiochromeno[4, 3-b]furan-4-ones, carbenes, 4-hydroxythiocoumarin, pyridinium ylides, 4H, 5H-thiochromeno[4, 3-b]pyran-5-ones, zirconium(IV) chloride, zinc, zinc carbenoids, multicomponent reactions, reductive rearrangement.

Abstract

Three-component condensation of in situ generated pyridinium acyl methylides with aromatic aldehydes and 4-hydroxythiocoumarin led to a series of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones. The reaction proceeds diastereoselectively with the formation of trans-isomers and represents a cascade process involving the Knoevenagel condensation, carbo-Michael reaction, and intramolecular nucleophilic substitution. The subsequent redox rearrangement of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones by the action of Zn and ZrCl4 grants access to 4H,5H-thiochromeno[4,3-b]pyran-5-ones.

 

Author Biographies

Максим Р. Демидов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

к.х.н, научный сотрудник кафедры органической химии

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

к.х.н., доцент кафедры органической химии

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

Published

2021-05-26

Issue

Section

Original Papers