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

Soukaina Alaoui; Mohsine Driowya; Luc Demange; Rachid Benhida; Khalid Bougrin

doi:10.1016/j.ultsonch.2017.07.019

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 Jan;40(Pt A):289-297. doi: 10.1016/j.ultsonch.2017.07.019. Epub 2017 Jul 11.

Authors

Soukaina Alaoui¹, Mohsine Driowya¹, Luc Demange², Rachid Benhida³, Khalid Bougrin⁴

Affiliations

¹ Laboratoire de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Université Mohammed V, Faculté des Sciences, B.P. 1014 Rabat, Morocco.
² Université Côte d'Azur, Institut de Chimie de Nice, ICN, UMR CNRS 7272, 28 avenue de Valrose, 06108 Nice Cedex 2, France; Département de Chimie, Université Paris Descartes, Sorbonne Paris Cité, UFR des Sciences Pharmaceutiques, 4 avenue de l'Observatoire & UFR Biomédicale des Saints Pères, 45 rue des Saints Pères, 75006 Paris, France.
³ Université Côte d'Azur, Institut de Chimie de Nice, ICN, UMR CNRS 7272, 28 avenue de Valrose, 06108 Nice Cedex 2, France.
⁴ Laboratoire de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Université Mohammed V, Faculté des Sciences, B.P. 1014 Rabat, Morocco. Electronic address: kbougrin@yahoo.fr.

PMID: 28946427
DOI: 10.1016/j.ultsonch.2017.07.019

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.

Keywords: 3,5-Disubstituted isoxazoles; Aqueous medium; CAN; Sulfonamides; Ultrasound irradiation.