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Please login or sign up for a free trial to access the full content. Method 8: Synthesis from Alkylidenemalononitriles and Compounds Containing a CH-Acidic Group

DOI: 10.1055/sos-SD-024-00566

Kantlehner, W.Science of Synthesis, (200624576.

Compounds containing an amino group in a β-position with respect to a CH-acidic group undergo a vinylogous addition to alkylidenemalononitriles in the presence of a base. The amino group in the adduct formed, can undergo reaction with a δ-nitrile group to effect an intramolecular cyclization, possibly via tautomeric intermediates, to give heterocyclic ketene N,N-acetals. Usually, ethanol or acetonitrile is used as solvent and piperidine as the base (Scheme 12).

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