Please use this identifier to cite or link to this item: https://doi.org/10.1039/c3gc36966h
Title: Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines
Authors: Ang, W.J.
Chu, C.-Y.
Chou, T.-C.
Lo, L.-C.
Lam, Y. 
Issue Date: Mar-2013
Citation: Ang, W.J., Chu, C.-Y., Chou, T.-C., Lo, L.-C., Lam, Y. (2013-03). Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines. Green Chemistry 15 (3) : 780-785. ScholarBank@NUS Repository. https://doi.org/10.1039/c3gc36966h
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. This journal is © 2013 The Royal Society of Chemistry.
Source Title: Green Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/75593
ISSN: 14639262
DOI: 10.1039/c3gc36966h
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