Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure–ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine?

Organic & Biomolecular Chemistry Pub Date: 2016-02-04 DOI: 10.1039/C5OB02596F

Abstract

A convenient general approach to 2-(pyrazol-4-yl)- and 2-(isoxazol-4-yl)ethanols based on the Br?nsted acid-initiated reaction of 3-acyl-4,5-dihydrofurans with hydrazines or hydroxylamine was developed. Further transformation of the alcohol moiety in 2-(pyrazolyl)ethanols affording 2-(pyrazolyl)ethylamine as potent bioactive compounds as well as pyrazole-substituted derivatives of antitumor alkaloid crispine A was elaborated.

Graphical abstract: Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure–ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine
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