Cu(II) /TEMPO-promoted one-pot synthesis of highly substituted pyrimidines from amino acid esters.
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 N-C 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.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P. R. China).
Nini
N
Zhou
Tao
T
Xie
Zhongle
Z
Li
Zhixiang
Z
Xie
D000596:Amino Acids / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003500:Cyclization; D004952:Esters; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D003497:Cyclic N-Oxides; D004952:Esters; D011743:Pyrimidines; D003300:Copper; C003959:TEMPO
amino acid esters; copper; pyrimidines; radical reactions; reaction mechanisms