Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 57, Issue 5, Pages 568-573Publisher
SPRINGER
DOI: 10.1007/s10593-021-02944-0
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
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Funding
- Russian Foundation for Basic Research [19-03-01024]
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The three-component condensation reaction involving in situ generated pyridinium acyl methylides with aromatic aldehydes and 4-hydroxythiocoumarin resulted in the synthesis of a series of novel compounds. The reaction proceeds through a cascade process including multiple consecutive steps and has significant experimental value.
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.
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