Synthesis of Cyclohepta[<i>b</i>]indoles and Furo[3,4-<i>b</i>]carbazoles from Indoles, Tertiary Propargylic Alcohols, and Activated Alkynes
Haiting Yin, Yunjun Wu, Yifan Jiang, Meifang Wang, Shaoyin Wang
Abstract
A robust metal-free and environmentally friendly approach to cyclohepta[ b ]indole and furo[3,4- b ]carbazole frameworks via a three-component reaction from indoles, tertiary propargylic alcohols, and activated alkynes is described. A probable mechanism was proposed on the basis of the isolation and characterization of a key intermediate of the reaction. A gram-scale reaction and product derivatizations were also performed to demonstrate the practicality of the developed methodology.
Topics & Concepts
ChemistryIndole testCarbazoleCombinatorial chemistryEnvironmentally friendlyStereochemistryMedicinal chemistryOrganic chemistryEcologyBiologyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsSulfur-Based Synthesis Techniques