Issue 10, 2012
From the journal:

Organic & Biomolecular Chemistry

One-step synthesis of differently bis-functionalized isoxazoles by cycloaddition of carbamoylnitrile oxide with β-keto esters†

Nagatoshi Nishiwaki,*a   Kazuya Kobiro,a   Shotaro Hirao,a   Jun Sawayama,a   Kazuhiko Saigo,a   Yumiko Ise,b   Maho Nishizawab  and  Masahiro Arigab  

* Corresponding authors

a School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada Kami, Kochi, Japan
E-mail: nishiwaki.nagatoshi@kochi-tech.ac.jp
Fax: +81 887 57 2520
Tel: +81 887 57 2517

b Department of Chemistry, Osaka Kyoiku University, Asahigaoka, Kashiwara, Osaka, Japan

Abstract

A new protocol for synthesizing different functionalized isoxazoles is provided. Carbamoylnitrile oxide generated from nitroisoxazolone underwent inverse electron-demand 1,3-dipolar cycloaddition with 1,3-dicarbonyl compounds in the presence of magnesium acetate that formed magnesium enolatein situ. Although electron-deficient trifluoroacetoacetate did not undergo this cycloaddition under the same conditions, conversion to sodium enolate furnish the corresponding bis-functionalized trifluoromethylisoxazole. The DFT calculations using B3LYP 6-31G+(d,p) also supported the aforementioned reactivity.

Graphical abstract: One-step synthesis of differently bis-functionalized isoxazoles by cycloaddition of carbamoylnitrile oxide with β-keto esters

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Article information

DOI
https://doi.org/10.1039/C2OB06925C
Article type
Paper
Submitted
15 Nov 2011
Accepted
19 Dec 2011
First published
27 Jan 2012

Org. Biomol. Chem., 2012,10, 1987-1991

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One-step synthesis of differently bis-functionalized isoxazoles by cycloaddition of carbamoylnitrile oxide with β-keto esters

N. Nishiwaki, K. Kobiro, S. Hirao, J. Sawayama, K. Saigo, Y. Ise, M. Nishizawa and M. Ariga, Org. Biomol. Chem., 2012, 10, 1987 DOI: 10.1039/C2OB06925C

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