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Water Promoted One-pot Three-Step Synthesis of Novel N-Saccharin Isoxazolines/Isoxazoles Using KI/Oxone Under Ultrasonic Activation

[ Vol. 23 , Issue. 11 ]

Author(s):

Hamza Tachallait, Mohsine Driowya, Eleuterio Álvarez, Rachid Benhida and Khalid Bougrin*   Pages 1254 - 1265 ( 12 )

Abstract:


A green and efficient regioselective protocol was developed for the preparation of novel isoxazolines and isoxazoles of N-saccharin derivatives via the water-promoted cycloaddition reaction of nitrile oxides with alkenes and alkynes. It is noteworthy that KI/Oxone/water-promoted one-pot three-component reactions of aldehyde, hydroxylamine hydrochloride, and alkene or alkyne were observed to be very satisfactory. The synthesis of all adducts (4a-j/5a-j) has been carried out by this method with high to excellent yields (70-95%) at 25°C within 30 min, using ultrasonic probe. All the new compounds were thoroughly characterized by spectroscopic techniques and also 5b, 5c and 5f were structurally identified by single-crystal X-ray diffraction methods. X-ray crystallography structure analysis clearly supported the regioselectivity of the cycloaddition reaction.

Keywords:

One-pot synthesis, N-saccharin isoxazolines, N-saccharin isoxazoles, green chemistry, ultrasound irradiation, alkynes.

Affiliation:

Department of Chemistry, Equipe de Chimie des Plantes et de SynthÃ�¨se Organique et Bioorganique, URAC23, Faculty of Science, B.P. 1014, GEOPAC Research Center, Mohammed V University, Rabat, Department of Chemistry, Equipe de Chimie des Plantes et de SynthÃ�¨se Organique et Bioorganique, URAC23, Faculty of Science, B.P. 1014, GEOPAC Research Center, Mohammed V University, Rabat, Instituto de Investigaciones Químicas, CSICUniversidad de Sevilla, Avda. Américo Vespucio, 49, Isla de La Cartuja, 41092 Sevilla, Université Côte d’Azur, CNRS, Institut de Chimie de Nice UMR 7272, 06108 Nice, Department of Chemistry, Equipe de Chimie des Plantes et de SynthÃ�¨se Organique et Bioorganique, URAC23, Faculty of Science, B.P. 1014, GEOPAC Research Center, Mohammed V University, Rabat



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