Issue 30, 2017

Rapid and selective synthesis of spiropyrazolines and pyrazolylphthalides employing Seyferth–Gilbert reagent

Abstract

An unexpected product-selectivity in the reaction of 2-arylideneindane-1,3-dione with dimethyl diazomethylphosphonate leading to the formation of two different types of products is reported. The reaction carried out in acetone in the presence of catalytic amount of cesium fluoride afforded spiropyrazoline phosphonates via 1,3-dipolar cycloaddition reaction, whereas the reaction in methanol yielded an interesting class of pyrazolylphthalides. This strategy provides an efficient alternative method for the construction of pyrazolylphthalides, and moreover, the process is general, works under mild conditions, and exhibits high functional group compatibility.

Graphical abstract: Rapid and selective synthesis of spiropyrazolines and pyrazolylphthalides employing Seyferth–Gilbert reagent

Supplementary files

Article information

Article type
Paper
Submitted
12 Jun 2017
Accepted
15 Jul 2017
First published
17 Jul 2017

Org. Biomol. Chem., 2017,15, 6411-6415

Rapid and selective synthesis of spiropyrazolines and pyrazolylphthalides employing Seyferth–Gilbert reagent

A. K. Gupta, N. K. Vaishanv, R. Kant and K. Mohanan, Org. Biomol. Chem., 2017, 15, 6411 DOI: 10.1039/C7OB01417A

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