Issue 4, 2013
From the journal:

Organic & Biomolecular Chemistry

Direct construction of 5-methyl-2-phenylisoxazol-3(2H)-ones via hypervalent iodine mediated sequential tandem oxidative cyclization of 3-oxo-N-phenylbutanamides catalyzed by zinc oxide (ZnO)†

Weibing Liu,*a   Peng Zhou,a   Cui Chen,a   Qing Zhanga  and  Zhibo Zhu*b  

* Corresponding authors

a School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, 139 of Guangdu Two Road, Maoming 525000, P. R. China
E-mail: lwb409@yahoo.com.cn
Fax: +86-668-2923575
Tel: +86-668-2923956

b School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China
E-mail: zzb24@yahoo.com.cn

Abstract

A sequential oxidative tandem cyclization reaction mediated by a combination of (diacetoxyiodo)benzene (DIB) with zinc oxide (ZnO) is presented for the synthesis of 5-methyl-2-phenylisoxazol-3(2H)-ones from β-ketobutylanilides. A variety of β-ketobutylanilide compounds were used in this approach, and a wide range of functionalized 5-methylisoxazol-3(2H)-ones were obtained in good to excellent yields.

Graphical abstract: Direct construction of 5-methyl-2-phenylisoxazol-3(2H)-ones via hypervalent iodine mediated sequential tandem oxidative cyclization of 3-oxo-N-phenylbutanamides catalyzed by zinc oxide (ZnO)

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Article information

DOI
https://doi.org/10.1039/C2OB27145A
Article type
Communication
Submitted
04 Nov 2012
Accepted
22 Nov 2012
First published
26 Nov 2012

Org. Biomol. Chem., 2013,11, 542-544

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Direct construction of 5-methyl-2-phenylisoxazol-3(2H)-ones via hypervalent iodine mediated sequential tandem oxidative cyclization of 3-oxo-N-phenylbutanamides catalyzed by zinc oxide (ZnO)

W. Liu, P. Zhou, C. Chen, Q. Zhang and Z. Zhu, Org. Biomol. Chem., 2013, 11, 542 DOI: 10.1039/C2OB27145A

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