Synthesis of Tetrahydroindolizino[8,7-<i>b</i>]indole Derivatives in the Presence of Fe(OTf)<sub>3</sub> or CF<sub>3</sub>SO<sub>3</sub>H through Intramolecular Dearomatization of Indole
Hai‐Lei Cui, Si‐Wei Liu, Xue Xiao
Abstract
We have developed a convenient synthesis of tetrahydroindolizino[8,7-b]indole derivatives via intramolecular dearomatization of indole. Highly functionalized tetrahydroindolizinoindoles can be prepared in the presence of trifluoromethanesulfonic acid in good to excellent yields (up to >99% yield) with novel designed pyrrole-tethered indoles. The same products can also be synthesized through a mild Fe(OTf)3-catalyzed process in acceptable to good yields (up to 75% yield).
Topics & Concepts
ChemistryIndole testIntramolecular forceYield (engineering)PyrroleCombinatorial chemistryMedicinal chemistryOrganic chemistryStereochemistryMetallurgyMaterials scienceCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Characterization of Pyrroles