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


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Output type: Journal article

UM6P affiliated Publication?: Yes

Author list: Tachallait, Hamza; Driowya, Mohsine; Alvarez, Eleuterio; Benhida, Rachid; Bougrin, Khalid

Publisher: Bentham Science Publishers

Publication year: 2019

Journal: Current Organic Chemistry (1385-2728)

Volume number: 23

Issue number: 11

Start page: 1270

End page: 1281

Number of pages: 12

ISSN: 1385-2728

Languages: English (EN-GB)


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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 nitrite 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 degrees 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.


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Last updated on 2021-21-11 at 23:16