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Cu II /TEMPO‐Promoted One‐Pot Synthesis of Highly Substituted Pyrimidines from Amino Acid Esters
Author(s) -
Zhou Nini,
Xie Tao,
Li Zhongle,
Xie Zhixiang
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405447
Subject(s) - dehydrogenation , yield (engineering) , chemistry , imine , cycloaddition , amino acid , oxidative phosphorylation , organic chemistry , combinatorial chemistry , catalysis , biochemistry , materials science , metallurgy
A novel, Cu(OAc) 2 /TEMPO promoted one‐step approach for the preparation of fully substituted pyrimidines from readily available amino acid esters has been described. In this reaction, the amino acid esters act as the only NC sources for the construction of corresponding pyrimidines. The mechanism of this process includes oxidative dehydrogenation, the generation of an imine radical, and a formal [3+3] cycloaddition. This methodology proves to be a high atom‐economic and straightforward strategy for the synthesis of pyrimidines and diverse substrates which are substituted by various functional groups have been afforded in moderate to good yield.