A facile and general acid-catalyzed deuteration at methyl groups of N-heteroarylmethanes

被引:44
|
作者
Liu, Min [1 ]
Chen, Xue [1 ]
Chen, Tieqiao [1 ]
Yin, Shuang-Feng [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
关键词
C-H ACTIVATION; H/D EXCHANGE; ACRIDONE ALKALOIDS; DISCOVERY; DEUTERIUM; INHIBITORS; QUINAZOLINE; OXIDATION; QUINOLINE; BONDS;
D O I
10.1039/c7ob00062f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and general Bronsted acid-catalyzed deuteration at the methyl group of N-heteroarylmethanes was achieved through a dearomatic enamine intermediate under relatively mild reaction conditions. Both 2-methyl and 4-methyl groups in quinolines were deuterated with high deuterium incorporation. Pyridines, benzo[d] thiazoles, indoles and imines including these clinical drugs were also deuterated efficiently at the methyl groups. This reaction could be conducted on a large scale (500 mmol), showing its good potential for use in large-scale synthesis.
引用
收藏
页码:2507 / 2511
页数:5
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