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Unexpected Aldehyde-Catalyzed Reaction of Imidazole N-Oxides with Ethyl Cyanoacetate

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The reaction of 2-unsubstituted imidazole N-oxides with ethyl cyanoacetate and aromatic aldehydes leads to the formation of ethyl 2-cyano-2-(1,3-dihydro-2H-imidazole-2-ylidene)acetates. The reaction proceeds through an initial [3+2] cycloaddition, followed by cleavage… Click to show full abstract

The reaction of 2-unsubstituted imidazole N-oxides with ethyl cyanoacetate and aromatic aldehydes leads to the formation of ethyl 2-cyano-2-(1,3-dihydro-2H-imidazole-2-ylidene)acetates. The reaction proceeds through an initial [3+2] cycloaddition, followed by cleavage of the cycloadduct and regeneration of the aldehyde, which essentially plays a catalytic role.

Keywords: ethyl cyanoacetate; aldehyde catalyzed; unexpected aldehyde; imidazole oxides; reaction; oxides ethyl

Journal Title: Synlett
Year Published: 2019

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