BF3-Mediated C2-Amidation of Quinoline N-Oxides Employing Trifluorodiazoethane and Acetonitrile: Access to 2-N-(Trifluoroethyl)amidoquinolines

被引：0
作者：
Dhami, Anamika [1 ]
Chandrasekharan, Sanoop P. [1 ]
Mohanan, Kishor [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
来源：
ORGANIC LETTERS | 2024年 / 27卷 / 01期
关键词：
TRIFLUOROMETHYL DIAZOMETHANE; AMINATION; FLUORINE; CF3CHN2; 2,2,2-TRIFLUORODIAZOETHANE; ACTIVATION; NITRILES; SCAFFOLD;
D O I：
10.1021/acs.orglett.4c04127
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Lewis acid-mediated C2-N-trifluoroethylamidation of quinolines, employing quinoline N-oxides, trifluorodiazoethane, and acetonitrile to forge a new class of N-(quinolin-2-yl)-N-(trifluoroethyl)acetamide is presented in this Letter. The reaction proceeds through a carbene generation/nitrile ylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish quinoline-2-N-(trifluoroethyl)acetamide derivatives in high yields.
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页码：180 / 185
页数：6
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