Victory, P.
Alvarezlarena, A.
Germain, Gabriel
[UCL]
Kessels, R.
Piniella, JF.
Vidalferran, A.
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.
Bibliographic reference |
Victory, P. ; Alvarezlarena, A. ; Germain, Gabriel ; Kessels, R. ; Piniella, JF. ; et. al. A Non-obvious Reaction Pathway in the Formation of 2-aminobenzene-1,3-dicarbonitriles From Alpha,Beta-unsaturated Ketones Or Aldehydes. In: Tetrahedron, Vol. 51, no. 1, p. 235-242 (1995) |
Permanent URL |
http://hdl.handle.net/2078.1/48319 |