NEW REACTIONS OF AMINO-FUNCTIONALIZED 3-VINYL-1H-INDOLES AND TETRAHYDROPYRIDIN-4-YL ANALOGS WITH DIENOPHILES

Reactions of 3-[2-(morpholin-4-yl)vinyl]-1H-indole (1), the 1,2-dihydro-9H-carbazole 2, as well as the 3-(tetrahydropyridin-4-yl)-1H-indoles 3a and 3b with some carbo- and heterodienophiles are described. The scope and limitations of the synthetic utility of these amino- (or homoamino)-functionalized 3-vinyl-1H-indoles are reported and some MO calculations for the qualitative prediction of their reactivities are presented. The reactions gave rise to substitution products, redox products, Diels-Alder adducts, ene adducts, and Michael-type adducts (Schemes 2 and 3).