Reactions of carbanions from 2-(dialkylamino)-arylacetonitriles with acetylene - Simple syntheses of 1,3-dienamines and 1,4-diketones

Article abstract of DOI:10.1016/S0040-4020(01)81381-8

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 1,4-diarylbutan-1,4-diones 8 in high yields.