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A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system

Author:
Jiang, Xiaoying, Xu, Xiaohe, Lin, Yuyan, Yan, Yiyan, Li, Pingping, Bai, Renren, Xie, Yuanyuan
Source:
Tetrahedron 2018 v.74 no.40 pp. 5879-5885
ISSN:
0040-4020
Subject:
aldehydes, byproducts, carbonyl compounds, chemical reactions, ketones, medicinal properties, moieties, oximes, phthalic acid
Abstract:
An efficient method for synthesis of oximes from aldehydes or ketones with N-hydroxyphthalimide or N-hydroxysuccinimide in water has been described. It is the first time to utilize NHPI as an oximation reagent to synthesize aldoximes and ketoximes from the corresponding organic carbonyl compounds without other reagents. The reaction tolerates various functional groups and affords the corresponding oximes in 76%–98% yields. The by-product phthalic acid can be recycled from the system. In addition, this method has been successfully applied to the synthesis of the precursor of some pharmacologically active amide molecules.
Agid:
6129400