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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

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

Author(s): Hamza Tachallait, Mohsine Driowya, Eleuterio Álvarez, Rachid Benhida and Khalid Bougrin*

Volume 23, Issue 11, 2019

Page: [1270 - 1281] Pages: 12

DOI: 10.2174/1385272823666190621115726

Price: $65

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.

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