Copper-Catalyzed 8-Amido Chelation-Induced Remote C-H Amination of Quinolines

被引:86
作者
Sahoo, Harekrishna [1 ]
Reddy, Mallu Kesava [1 ]
Ramakrishna, Isai [1 ]
Baidya, Mahiuddin [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India
关键词
amination; azo compounds; C-H activation; copper; homogeneous catalysis; BOND ACTIVATION; N-OXIDES; DIRECT ARYLATION; DIRECT ALKYLATION; ALPHA-AMINATION; PALLADIUM; FUNCTIONALIZATION; DERIVATIVES; PYRIDINES; 8-AMINOQUINOLINES;
D O I
10.1002/chem.201504207
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-catalyzed 8-amide chelation-induced remote C-H amination of quinolines has been developed. This direct amination with readily available azodicarboxylates proceeded with perfect C5-regioselectivity offering amino-substituted 8-aminoquinolines, important bioactive molecular scaffolds, in very high yields (up to 96 %). A single-electron transfer (SET)-mediated mechanism with k(H)/k(D)=1.1 was proposed after trapping of the radical intermediate.
引用
收藏
页码:1592 / 1596
页数:5
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