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Selective Synthesis of Substituted Pyridines and Pyrimidines through Cascade Annulation of Isopropene Derivatives

Jian Li, Jiaming Li, Runfa He, Jiasheng Liu, Yang Liu, Lu Chen, Yubing Huang, Yibiao Li

2022Organic Letters25 citationsDOI

Abstract

Diverse substituted pyridines and pyrimidines with high selectivity were obtained using a concise and efficient protocol developed herein. The reaction proceeds via metal-free cascade annulation of isopropene derivatives. Using isopropene derivatives as C3 synthons, NH4I as the “N” source, and formaldehyde or dimethyl sulfoxide as the carbon source, this reaction realizes the efficient formation of intermolecular C–N and C–C bonds.

Topics & Concepts

AnnulationChemistrySynthonCascadeIntermolecular forceCombinatorial chemistryCascade reactionSelectivityFormaldehydeMoleculeOrganic chemistryCatalysisChromatographyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions