Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines

doi:10.1039/C3GC36966H

Paper

Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines

Published Feb 25, 2013 · W. Ang, Chi-Yuan Chu, Tzyy-Chao Chou

Green Chemistry

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7

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Abstract

A microwave-assisted, fluorous synthetic route to 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines has been developed. The strategy comprises linking the respective 2-fluorobenzonitrile or 2-(bromomethyl)benzonitrile to a fluorous oxime tag to give an aryloxime intermediate which then undergoes cyclization with concomitant cleavage of the substrate-tag in acidic conditions to provide the desired product in good to moderate yields. In addition, the aryloxime intermediate could be subjected to further reactions to expand the compound library. The product could be easily separated using fluorous solid-phase extraction (F-SPE) and the fluorous ketone recovered could be converted back to the fluorous oxime and reused in the next run of the synthesis.

Study Snapshot

This microwave-assisted, fluorous synthetic route provides efficient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines, with potential for further reactions and reuse of fluorous oxime.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines

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