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:
xuxp
suda.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
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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
ID: J42-Y2017
