Synthesis of Tetrahydro-5<i>H</i>-indolo[2,3-<i>b</i>]quinolines through Copper-Catalyzed Cascade Reactions of Aza-<i>o</i>-quinone Methides with Indoles
Dong-Liu Lu, Yi-Yun Yao, Yu‐Feng Liang, Cui Liang, Lu Lei, Lu Ma, Dong‐Liang Mo
Abstract
A variety of tetrahydro-5H-indolo[2,3-b]quinolines were prepared in 40–97% yields through a copper(II)-catalyzed cascade reaction of aza-o-quinone methides generated in situ from 2-(chloromethyl)anilines and indoles. Experimental results showed that the reaction underwent double 1,4-additions and sequential intramolecular cyclization. The present method features broad substrate scope, good functional group tolerance, and easy gram scalable preparation of indolo[2,3-b]quinolines.
Topics & Concepts
ChemistryCatalysisCascadeQuinoneCopperCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryChromatographySynthesis of Indole DerivativesSynthesis and bioactivity of alkaloidsAxial and Atropisomeric Chirality Synthesis