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

The Journal of Organic Chemistry
Vaijinath ManeIrishi N N Namboothiri

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 SN2'-intramolecular Michael reaction, followed by aromatization. The gram-scale synthesis of a representative example of sulfonylfurans was carried out to demonstrate the synthetic efficiency of the methodology.

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Citations

Apr 23, 2021·Organic & Biomolecular Chemistry·Raju Jannapu ReddyJangam Jagadesh Kumar
Jul 28, 2020·Organic Letters·Babasaheb Sopan GoreJeh-Jeng Wang

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