PhI(OAc)2-mediated oxidative rearrangement of allylic amides: efficient synthesis of oxazoles and β-keto amides

Kang Xu; Shuang Yang; Zhenhua Ding

doi:10.1039/C9QO01298B

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PhI(OAc)₂-mediated oxidative rearrangement of allylic amides: efficient synthesis of oxazoles and β-keto amides†

Kang Xu,^a Shuang Yang^a and Zhenhua Ding

*^a

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* Corresponding authors

^a Jiangsu Key Laboratory of Drug Design and Optimization, Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 211198, China
E-mail: zhding@cpu.edu.cn

Abstract

A series of 2,5-disubstituted oxazoles and β-keto amides were synthesized from allylic amides via PhI(OAc)₂-mediated intramolecular cyclization and oxidation with the migration of an aryl group. These reactions were performed under mild conditions with good functional group tolerance and gave the corresponding products in good to excellent yields.

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Article information

DOI: https://doi.org/10.1039/C9QO01298B
Article type: Research Article
Submitted: 24 Oct 2019
Accepted: 14 Nov 2019
First published: 15 Nov 2019

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Org. Chem. Front., 2020,7, 69-72

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PhI(OAc)₂-mediated oxidative rearrangement of allylic amides: efficient synthesis of oxazoles and β-keto amides

K. Xu, S. Yang and Z. Ding, Org. Chem. Front., 2020, 7, 69 DOI: 10.1039/C9QO01298B

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