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

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Unexpected Aldehyde-Catalyzed Reaction of Imidazole N-Oxides with Ethyl Cyanoacetate
Synlett ( IF 1.7 ) Pub Date : 2019-11-29 , DOI: 10.1055/s-0039-1691527
Anton V. Kutasevich ₁ , Anna S. Efimova ₁ , Marina N. Sizonenko ₁ , Valery P. Perevalov ₁ , Ludmila G. Kuz’mina ₂ , Vitaly S. Mityanov _{1,

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Affiliation

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.

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