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Synthesis of Densely Substituted Sulfonylfurans and Dihydrofurans via Cascade Reactions of α-Functionalized Nitroalkenes with β-Ketosulfones

Authors :
Adilson Beatriz
Vaijinath Mane
Sudheesh T. Sivanandan
Eufrânio N. da Silva Júnior
Rafael G. Santana
Irishi N. N. Namboothiri
Source :
The Journal of Organic Chemistry. 85:8825-8843
Publication Year :
2020
Publisher :
American Chemical Society (ACS), 2020.

Abstract

The reaction of β-ketosulfones with different α-functionalized nitroalkenes affords diversely substituted sulfonylfurans and dihydrofurans. Furthermore, β-ketosulfones react with α-bromonitroalkenes and α-hydrazinonitroalkenes via a cascade Michael addition-cyclization protocol to afford nitrodihydrofurans and hydrazinodihydrofurans, respectively, bearing a key sulfonyl group, in excellent yields with a broad substrate scope. Application of these products has been demonstrated by the synthesis of pyrroles and pyrazoles in good yields. The reaction of β-ketosulfones with nitroallylic acetates yields tetrasubstituted sulfonyl furans through a cascade S

Details

ISSN :
15206904 and 00223263
Volume :
85
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....9655725147ac68284bfcd9a6e4942cae
Full Text :
https://doi.org/10.1021/acs.joc.0c00606