A Non-obvious Reaction Pathway in the Formation of 2-aminobenzene-1,3-dicarbonitriles From Alpha,Beta-unsaturated Ketones Or Aldehydes
(1995) Tetrahedron — Vol. 51, n° 1, p. 235-242 (1995)
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- Abstract
- Key intermediates demonstrating a non-obvious reaction pathway leading to 2-aminobenzene-1,3-dicarbonitriles from enones have been isolated and characterised in tire reaction between (E)-4-phenyl-3-butene-2-one and propanedinitrile in a basic hydro-alcoholic medium. (E)-4-Phenyl-3-butene-2-one reacts with three molecules of propanedinitrile to give a 6-amino-2-iminobicyclo[2.2.2]-5-octene-1,3,3,5-tetracarbonitrile system which evolves to a substituted cyclohexadiene by elimination of the sodium salt of 1,1,1-tricyanomethane. Further oxidation leads to the final 2-aminobenzene-1,3-dicarbonitrile. The proposed pathway involves more steps and more difficult transformations than previously presented for similar systems. We can not exclude a simpler reaction pathway derived from the double Michael and Knoevenagel adduct of (E)-4-phenyl-3-butene-2-one and propanedinitrile, however we have not found any evidence for this simpler process.
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Citations
Victory, P., Alvarezlarena, A., Germain, G., Kessels, R., Piniella, JF., & Vidalferran, A. (1995). A Non-obvious Reaction Pathway in the Formation of 2-aminobenzene-1,3-dicarbonitriles From Alpha,Beta-unsaturated Ketones Or Aldehydes. Tetrahedron, 51(1), 235-242. https://doi.org/10.1016/0040-4020(94)00937-P (Original work published 1995)