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In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles

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Abstract

Herein, we present a novel [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-butyl nitrite. This three-component reaction provides new methodology for the direct synthesis of fully substituted isoxazole derivatives, featuring mild reaction conditions, readily accessible starting materials and simple operation. The experimental studies and DFT calculations suggest that the reaction starts with the generation of the key intermediate nitrile oxides, followed by a [3 + 2] cycloaddition reaction of β-keto esters to give the final isoxazole products.

Graphical abstract: In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles

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Publication details

The article was received on 08 May 2018, accepted on 03 Jun 2018 and first published on 04 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01067F
Citation: Org. Biomol. Chem., 2018, Advance Article
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    In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles

    R. Chen, A. A. Ogunlana, S. Fang, W. Long, H. Sun, X. Bao and X. Wan, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01067F

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