Organic Chemistry Portal



Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines

Xue-Qiang Chu, Wen-Bin Cao, Xiao-Ping Xu* and Shun-Jun Ji*

*College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China, Email:,

X.-Q. Chu, W.-B. Cao, X.-P. Xu, S.-J. Ji, J. Org. Chem., 2017, 82, 1145-1154.

DOI: 10.1021/acs.joc.6b02767

see abstract for more reactions


An operationally simple, regioselective reaction of ketones, aldehydes, or esters with amidines in the presence of TEMPO and an in situ prepared recyclable iron(II)-complex provides various pyrimidine derivatives with broad functional group tolerance. The reactions are likely to proceed through a TEMPO complexation/enamine addition/transient α-occupation/β-TEMPO elimination/cyclization sequence.

see article for more examples

proposed mechanism

Key Words

Pyrimidines, TEMPO

ID: J42-Y2017