Convenient Synthesis of 6,7,12,13-Tetrahydro-5 H -Cyclohepta[2,1- b :3,4- b' ]diindole Derivatives Mediated by Hypervalent Iodine (III) Reagent.

Bisindolyl alkaloids represent a large family of natural and synthetic products that display various biological activities. Among the bisindole compounds, 6,7,12,13-tetrahydro-5 H -cyclohepta[2,1- b :3,4- b' ]diindoles have received little attention. Only two methods have been developed for the construction of the 6,7,12,13-tetrahydro-5 H -cyclohepta[2,1- b :3,4- b' ]diindole scaffold thus far, including the classical Fischer indole synthesis conducted by reacting indole-fused cycloheptanone and hydrazines, and the condensation reaction to build the seven-membered ring. Here, we report for the first time a new route to synthesize 6,7,12,13-tetrahydro-5 H -cyclohepta[2,1- b :3,4- b' ]diindoles through intramolecular oxidative coupling of 1,3-di(1 H -indol-3-yl)propanes in the presence of PIFA, DDQ and TMSCl with moderate to excellent yields.