Xie Dianke, He Wei, Xiao Jiang, Wu Yao, Guo Yongjia, Liu Qiang, Guo Cancheng
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University Changsha 410082 P. R. China
RSC Adv. 2019 Mar 4;9(13):7203-7209. doi: 10.1039/c9ra00616h. eCollection 2019 Mar 1.
A convenient method for the synthesis of 2-oxo-acetamidines from methyl ketones using aromatic amines and DMF as nitrogen sources is reported copper-catalyzed C(sp)-H amidination. Various methyl ketones react readily with aromatic amines and DMF, producing 2-oxo-acetamidines in yields of 47 to 92%. This protocol features the simultaneous formation of C-N and C[double bond, length as m-dash]N bonds using DMF and aromatic amines as two different nitrogen sources. It thus provides an efficient approach to construct acyclic amidines three C(sp)-H bond amidination. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.
报道了一种使用芳香胺和DMF作为氮源，由甲基酮合成2-氧代脒的简便方法——铜催化的C(sp)-H amidination反应。各种甲基酮能很容易地与芳香胺和DMF反应，以47%至92%的产率生成2-氧代脒。该方法的特点是使用DMF和芳香胺作为两种不同的氮源同时形成C-N键和C=N键。因此，它为构建无环脒提供了一种有效的方法——通过三次C(sp)-H键amidination反应。基于初步实验，揭示了这种转化的一种可能机理。
