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Issue 10, 2012
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One-step synthesis of differently bis-functionalized isoxazoles by cycloaddition of carbamoylnitrile oxide with β-keto esters

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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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Publication details

The article was received on 15 Nov 2011, accepted on 19 Dec 2011 and first published on 27 Jan 2012


Article type: Paper
DOI: 10.1039/C2OB06925C
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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