Synthesis of 1,4-Dihydroquinolines and 4<i>H</i>-Chromenes via Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of <i>para</i>-Quinone Methides and Ynals
Junwei Wang, Quanjin Rong, Lei Zhao, Xiang Pan, Lin Zhao, Kun Zhao, Lihong Hu
Abstract
An organocatalytic domino aza/oxa-Michael/1,6-addition reaction of ortho-tosylaminophenyl or ortho-hydroxyphenyl-substituted para-quinone methides and ynals has been developed. In the presence of 20 mol % of morpholine, this unprecedented cascade reaction occurs readily in good yield (up to 99%), providing a highly efficient synthetic approach to synthetically valuable 1,4-dihydroquinolines and 4H-chromenes.
Topics & Concepts
ChemistryDominoMichael reactionYield (engineering)Cascade reactionMorpholineQuinoneOrganocatalysisOrganic chemistryCombinatorial chemistryCatalysisEnantioselective synthesisMaterials scienceMetallurgySynthesis of Indole DerivativesSynthesis of Organic CompoundsMulticomponent Synthesis of Heterocycles