First reactions of 2,2'-bisindolyls with electrophilic azo compounds and diethyl mesoxalate

Article abstract of DOI:10.1002/ardp.19923250609

Conformations and some electronic properties of the 2,2'-bisindolyls 6 were calculated for the prediction of probable Diels-Alder reactivity, in analogy to previous work on 2-vinylindoles. First reactions with dienophiles revealed that compounds 6 did not participate in [4 + 2]cycloadditions but rather underwent simple electrophilic substitutions at the enamine function with, above all, some heterodienophiles.