Issue 3, 2021
From the journal:

Organic Chemistry Frontiers

Switchable and efficient conversion of 2-amido-aryl oxazolines to quinazolin-4(3H)-ones and N-(2-chloroethyl)benzamides†

Weiqiang Chen,a   Mei Liu,b   Hui-Jing Li*ac  and  Yan-Chao Wu ORCID logo *a  

* Corresponding authors

a School of Marine Science and Technology, Weihai Marine Organism & Medical Technology Research Institute, Harbin Institute of Technology, Weihai 264209, P. R. China
E-mail: ycwu@iccas.ac.cn
Fax: (+86) 631-5688411

b China Building Material Test & Certification Group Zibo Co., Ltd., Zibo 255000, P. R. China

c Weihai Huiankang Biotechnology Co., Ltd, Weihai 264200, P. R. China

Abstract

Switchable chemoselective conversion of 2-amido-aryl oxazolines to quinazolin-4(3H)-ones or N-(2-chloroethyl)benzamides is achieved. The former reaction is proposed to involve a PIFA-mediated 6π electrocyclization followed by an in situ nucleophilic substitution, while the latter reaction uses aluminum chloride as a halogenated source through a ring-opening reaction. The reactions proceed smoothly under mild conditions and have excellent functional group compatibility.

Graphical abstract: Switchable and efficient conversion of 2-amido-aryl oxazolines to quinazolin-4(3H)-ones and N-(2-chloroethyl)benzamides

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Article information

DOI
https://doi.org/10.1039/D0QO01368D
Article type
Research Article
Submitted
03 Nov 2020
Accepted
30 Nov 2020
First published
08 Dec 2020

Org. Chem. Front., 2021,8, 584-590

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Switchable and efficient conversion of 2-amido-aryl oxazolines to quinazolin-4(3H)-ones and N-(2-chloroethyl)benzamides

W. Chen, M. Liu, H. Li and Y. Wu, Org. Chem. Front., 2021, 8, 584 DOI: 10.1039/D0QO01368D

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