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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: xuxpsuda.edu.cn, shunjunsuda.edu.cn

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 (free Supporting Information)



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Abstract

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.

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proposed mechanism



Key Words

Pyrimidines, TEMPO


ID: J42-Y2017