Three-component synthesis of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones and their reductive rearrangement into 4H,5H-thiochromeno[4,3-b]pyran-5-ones View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2021-05

AUTHORS

Maxim R. Demidov, Anastasiya N. Dobrokvashina, Dmitry V. Osipov, Vitaly А. Osyanin, Yuri N. Klimochkin

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. More... »

PAGES

568-573

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10593-021-02944-0

DOI

http://dx.doi.org/10.1007/s10593-021-02944-0

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1138609145


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