A ring transformation of isoxazole into 3,5-dicyano-4H-pyran-2-amines (4) and N-arylidenefuran-2-amines (7) is reported. It involves a ring opening of the isoxazole ring in the presence of an aromatic aldehyde, leading to 2-arylidene-3-oxopropanenitrile (2), followed by nucleophilic attack by either cyanide or propanedinitrile and then heterocyclization. The reaction can also be applied to 5-substituted isoxazoles.
J. A. Ciller, N. Martín, C. Seoane and J. L. Soto, J. Chem. Soc., Perkin Trans. 1, 1985, 2581 DOI: 10.1039/P19850002581
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