New Reactions of Amino‐Functionalized 3‐Vinyl‐1H‐indoles and Tetrahydropyridin‐4‐yl Analogues with Dienophiles

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Abstract
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).