Base-Promoted Three-Component Cascade Reaction of α-Hydroxy Ketones, Malonodinitrile, and Alcohols: Direct Access to Tetrasubstituted N<i>H</i>-Pyrroles
Hongjian Liu, Chaorong Qi, Lu Wang, Yanhui Guo, Dan Li, Huanfeng Jiang
Abstract
A base-promoted three-component cascade reaction of α-hydroxy ketones, malonodinitrile, and alcohols has been developed, providing a direct and efficient route to a range of structurally diverse and synthetically useful 2-alkyloxy-1H-pyrrole-3-carbonitrile derivatives. The reaction involved three different bond (C–C, C–O, and C–N) formations in a single step, and its regioselectivity was depended on the structure of the α-hydroxy ketones employed. The use of easily available starting materials, wide substrate scope, good functional group tolerance, operational simplicity, and high atom economy are attractive features of the new method.
Topics & Concepts
ChemistryAtom economyRegioselectivityCascadeSubstrate (aquarium)Cascade reactionCombinatorial chemistryComponent (thermodynamics)Base (topology)Reaction conditionsScope (computer science)PyrroleSimplicityKetoneFunctional groupCatalysisOrganic chemistryStereochemistryOceanographyEpistemologyComputer scienceMathematicsPhilosophyProgramming languageChromatographyMathematical analysisGeologyThermodynamicsPhysicsPolymerSynthesis and Characterization of PyrrolesCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods