The subject of this project is the study of condensation reaction of indole and ketone. Indole and indole derivatives are widely applied to material sciences, agrochemicals, and pharmaceuticals1. This research topic needs to be studied and supported by a large amount of date and hundreds of experiments, because the indole and ketone could be reacted in different solvents with different ratios and reaction conditions. For this limited-time UROP topic, which is also a small part of this huge project, two specific mole ratios are chosen for indole and ketones, which are 1:2 and 2:1 under acidic conditions. The emphasis is on the reaction of 2:1 indole and ketone reaction, in which the products are bisindolylmethanes (BIMs).
As an important class of indole derivatives, BIMs are “most active cruciferous substances for promoting beneficial estrogen metabolism and inducing apoptosis in human cancer cells” as written in Green Protocol for the Synthesis of Bisindolylmethanes and Evaluation of Their Antimicrobial Activities2. In this UROP project, the most straightforward method is chosen to synthesize BIMs, which is the acid-catalyzed condensation reaction of indole and ketones.