Synthesis p. 224 - 233 (1990)
Update date:2022-08-05
Topics:
Zdrojewski, T.
Jonczyk, A.
2-(Dialkylamino)arylacetonitriles 1 react with acetylenes 2a,b in dimethyl sulfoxide, powdered sodium hydroxide and triethylbenzylammonium chloride as a catalyst to give 3 and/or 4.The latter are formed via addition of anion 8 to immonium salt 9.The type of product formed depends on the basicity of amino moiety in 3.Furthermore, compound 1 adds to C-1 of acetylene 2c affording the vinyl derivatives 15.The products 3,4,11 and 15 are hydrolyzed to give ketones 5-7,12 and 16, respectively.
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