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

Title Ultrasound-assisted facile one-pot sequential synthesis of novel sulfonamide-isoxazoles using cerium (IV) ammonium nitrate (CAN) as an efficient oxidant in aqueous medium.
Authors S. Alaoui; M. Driowya; L. Demange; R. Benhida; K. Bougrin
Journal Ultrason Sonochem
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.

Citation S. Alaoui; M. Driowya; L. Demange; R. Benhida; K. Bougrin.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):289297. doi:10.1016/j.ultsonch.2017.07.019

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See more Cerium products. Cerium (atomic symbol: Ce, atomic number: 58) is a Block F, Group 3, Period 6 element with an atomic weight of 140.116. The number of electrons in each of cerium's shells is 2, 8, 18, 19, 9, 2 and its electron configuration is [Xe]4f2 6s2. Cerium Bohr ModelThe cerium atom has a radius of 182.5 pm and a Van der Waals radius of 235 pm. In its elemental form, cerium has a silvery white appearance. Cerium is the most abundant of the rare earth metals. It is characterized chemically by having two valence states, the +3 cerous and +4 ceric states. The ceric state is the only non-trivalent rare earth ion stable in aqueous solutions. Elemental CeriumIt is therefore strongly acidic and oxidizing, in addition to being moderately toxic.The cerous state closely resembles the other trivalent rare earths. Cerium is found in the minerals allanite, bastnasite, hydroxylbastnasite, monazite, rhabdophane, synchysite and zircon. Cerium was discovered by Martin Heinrich Klaproth, Jöns Jakob Berzelius, and Wilhelm Hisinger in 1803 and first isolated by Carl Gustaf Mosander in 1839. The element was named after the asteroid Ceres, which itself was named after the Roman god of agriculture.

Nitrogen

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