New Reactions of 3-Vinyl- and 3-(2-Propenyl)indoles with N- Phenylmaleimide: Cycloaddition, Ene Reaction, and Dimerization

Article abstract of DOI:10.1002/hlca.19880710220

Depending on the substitution pattern of the aminobutadiene subunit in the selected 3-vinylindoles 1, 3, 6, and 9, stereospecific <4+2> cycloadditions ("endo"-preference) and dimerizations take place on reaction with N- phenylmaleimide.In the reaction of 9 with N-phenylmaleimide in the absence of a Lewis-acid catalyst, a competing ene reaction occurs in addition to the Diels-Alder reaction.