Issue 4, 2011
From the journal:

Organic & Biomolecular Chemistry

Direct transition-metal-free intramolecular C–O bond formation: synthesis of benzoxazole derivatives†

Jinsong Peng,*a   Cuijuan Zong,a   Min Ye,a   Tonghui Chen,a   Dewei Gao,a   Yufeng Wanga  and  Chunxia Chen*a  

* Corresponding authors

a Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. China
E-mail: jspeng1998@163.com, ccx1759@163.com

Abstract

A direct base-mediated intramolecular carbon-oxygen bond formation has been developed without a transition-metal catalyst. In the presence of 2.0 equiv of K2CO3 in DMSO at 140 °C, the intramolecular cyclization of o-haloanilides affords benzoxazoles in high yields. A mechanism via an initial formation of a benzyne intermediate followed by nucleophilic addition to form the C–O bond has been proposed.

Graphical abstract: Direct transition-metal-free intramolecular C–O bond formation: synthesis of benzoxazole derivatives

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Article information

DOI
https://doi.org/10.1039/C0OB00454E
Article type
Paper
Submitted
19 Jul 2010
Accepted
03 Nov 2010
First published
24 Dec 2010

Org. Biomol. Chem., 2011,9, 1225-1230

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Direct transition-metal-free intramolecular C–O bond formation: synthesis of benzoxazole derivatives

J. Peng, C. Zong, M. Ye, T. Chen, D. Gao, Y. Wang and C. Chen, Org. Biomol. Chem., 2011, 9, 1225 DOI: 10.1039/C0OB00454E

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