Water Promoted One-pot Three-Step Synthesis of Novel N-Saccharin Isoxazolines/Isoxazoles Using KI/Oxone Under Ultrasonic Activation-Reference-Cited by-同舟云学术

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

Published:2019-08-29 Issue:11 Volume:23 Page:1270-1281
ISSN:1385-2728
Container-title:Current Organic Chemistry
language:en
Short-container-title:COC

Author:

Tachallait Hamza¹,Driowya Mohsine¹,Álvarez Eleuterio²,Benhida Rachid³,Bougrin Khalid¹

Affiliation:

1. Department of Chemistry, Equipe de Chimie des Plantes et de Synthese Organique et Bioorganique, URAC23, Faculty of Science, B.P. 1014, GEOPAC Research Center, Mohammed V University, Rabat, Morocco

2. Instituto de Investigaciones Quimicas, CSICUniversidad de Sevilla, Avda. Americo Vespucio, 49, Isla de La Cartuja, 41092 Sevilla, Spain

3. Universite Cote d'Azur, CNRS, Institut de Chimie de Nice UMR 7272, 06108 Nice, France

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.

Funder

COST Action

Campus France PHCToubkal

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry

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