Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium.

Author(s) Alaoui, S.; Driowya, M.; Demange, L.; Benhida, R.; Bougrin, K.
Journal Ultrason Sonochem
Date Published 2018 Jan
Abstract

A series of novel 3,5-disubstituted isoxazoles have been synthesized, using a new, green, and versatile "one-pot three-steps" methodology. The key step is an oxidative 1,3-dipolar cycloaddition under ultrasonic irradiation, occurring in aqueous media, and mediated by cerium (IV) ammonium nitrate (CAN). CAN is a one-electron oxidant, highly soluble in water, slightly toxic and inexpensive, that allows the in situ conversion of the intermediate aldoximes into nitrile oxide. The syntheses are highly regioselective, as illustrated by the structures of the final compounds, which have been fully assessed by spectral analyses (1H and 13C NMR, MS). This study illustrates the potency of the ultrasound activation to synthesize a set of highly functionalized heterocycles, with potential applications in biology, in short reaction times and following an eco-friendly process.

DOI 10.1016/j.ultsonch.2017.07.019
ISSN 1873-2828
Citation Alaoui S, Driowya M, Demange L, Benhida R, Bougrin K. Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium. Ultrason Sonochem. 2018;40(Pt A):289-297.

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