Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and <i>N</i>,<i>N</i>-Dimethylaminoethanol as One Carbon Donor
Zemin Qin, Yongmin Ma, Fanzhu Li
Abstract
An efficient, facile, and eco-friendly synthesis of pyrimidine derivatives has been developed. It involves a [3 + 2 + 1] three-component annulation of amidines, ketones, and one carbon source. N,N-Dimethylaminoethanol is oxidized through C(sp3)–H activation to provide the carbon donor. One C–C and two C–N bonds are formed during the oxidative annulation process. The reaction shows good tolerance to many important functional groups in air, making this methodology a highly versatile alternative, and significant improvement to the existing methods for structuring a pyrimidine framework, especially 4-aliphatic pyrimidines.
Topics & Concepts
AnnulationChemistryPyrimidineCarbon fibersOrganic chemistryCombinatorial chemistryMedicinal chemistryCatalysisStereochemistryMaterials scienceComposite numberComposite materialCatalytic C–H Functionalization MethodsQuinazolinone synthesis and applicationsMulticomponent Synthesis of Heterocycles