REACTIONS OF CARBANIONS FROM 2-(DIALKYLAMINO)-ARYLACETONITRILES WITH ACETYLENE SIMPLE SYNTHESES OF 1,3-DIENAMINES AND 1,4-DIKETONES

It has been found that morpholinonitrile 1a reacts with acetylene (2) in the presence of solid sodium hydroxide and tetrabutylammonium bromide (TBABr) as a catalyst, in DMSO, to give the vinyl derivative 3a. Whereas aminonitriles 1b-i, in the reaction with 2, afford dienamines 7. The different reactivity of 1a as compared to 1b-i is explained in terms of the different basicity of the amino moiety in vinyl derivatives 3. Dienamines 7 were hydrolyzed to l,4-diarylbutan-l,4-diones 8 in high yields. © 1990.