Journal
SYNLETT
Volume 31, Issue 2, Pages 179-182Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1691527
Keywords
imidazole oxides; 1,3-dipolar cycloaddition; reaction mechanism; organocatalysis; multicomponent reaction; [3+2] cycloaddition
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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 of the cycloadduct and regeneration of the aldehyde, which essentially plays a catalytic role.
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