A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system. Issue 40 (4th October 2018)

• Record Type: Journal Article
• Authors: Jiang, Xiaoying; Xu, Xiaohe; Lin, Yuyan; Yan, Yiyan; Li, Pingping; Bai, Renren; Xie, Yuanyuan
• Is Part Of: Tetrahedron. Volume 74:Issue 40(2018)
• Page Start: 5879
• Page End: 5885
• Publication Date: 2018-10-04
• Subjects: N-hydroxyphthalimide -- Oximation -- Aldoximes -- Ketoximes -- Phthalic acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.08.013
• Languages: English
• ISSNs: 0040-4020

Abstract

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. Graphical abstract: