Double Addition Reactions Involving Vinyl-Substituted N-Heterocycles and Active Methylene Compounds

A series of conjugate addition reactions have been performed with vinyl-substituted N-heterocycles in acid-catalyzed conversions. Using active methylene compounds, double conjugate addition reactions have been accomplished to provide dipyridyl and related heterocyclic products. These conversions have utilized 1,3-dicarbonyl compounds, cyano esters, a cyano sulfone, and malonyl nitrile as nucleophiles. The Michael accepting groups include vinyl-substituted pyridines, quinoline, and pyrazine. Double conjugate addition reactions have also been accomplished with 2,6-divinylpyridine and related systems.