Issue 5, 2015

Domino reaction involving the Bestmann–Ohira reagent and α,β-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles

Abstract

A mild, efficient and rapid domino reaction involving the Bestmann–Ohira reagent (BOR) and α,β-unsaturated aldehydes has been developed for the synthesis of densely functionalized vinylpyrazoles. This reaction demonstrates the dual reactivity of BOR as a homologation reagent as well as a cycloaddition partner, thus constituting a domino reaction in an operationally simple procedure. The application of this efficient synthesis of pyrazoles has been demonstrated for the synthesis of phosphonyl analogues of pyrrolopyrazole alkaloids.

Graphical abstract: Domino reaction involving the Bestmann–Ohira reagent and α,β-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles

Supplementary files

Article information

Article type
Paper
Submitted
07 Nov 2014
Accepted
25 Nov 2014
First published
25 Nov 2014

Org. Biomol. Chem., 2015,13, 1492-1499

Domino reaction involving the Bestmann–Ohira reagent and α,β-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles

S. Ahamad, A. K. Gupta, R. Kant and K. Mohanan, Org. Biomol. Chem., 2015, 13, 1492 DOI: 10.1039/C4OB02365J

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