Abstract Addition of an indole, which does not have a group at the 3-position, to 1, 4- naphthoquinone leads to the expected 2-(3-indolyl)-1, 4-naphthoquinone. When the 1, 4- naphthoquinone is substituted at the 2-position by an alkyl or aryl group, the 2-substituted 3- (3-indolyl)-1, 4-naphthoquinone is easily formed. However, when the 2-substituent of the quinone is functional (OH, OMe, CI, Br, NC 5 H 10, SC 6 H 5), in addition to the new series ...