Potassium tert-Butoxide-Mediated Synthesis of 2-Aminoquinolines from Alkylnitriles and 2-Aminobenzaldehyde Derivatives

被引:6
|
作者
Kishore, Pendyala Satya [1 ]
Gujjarappa, Raghuram [2 ]
Putta, V. P. Rama Kishore [1 ]
Polina, Saibabu [1 ]
Singh, Virender [3 ]
Malakar, Chandi C. [2 ]
Pujar, Prasad Pralhad [1 ]
机构
[1] CHRIST, Dept Chem, Bangalore 560029, India
[2] Natl Inst Technol Manipur, Dept Chem, Imphal 795004, Manipur, India
[3] Cent Univ Punjab, Dept Chem, Bathinda 151001, Punjab, India
来源
CHEMISTRYSELECT | 2022年 / 7卷 / 46期
关键词
Alkyl cyanides; (KOBu)-Bu-t; Transition-metal-free; 2-Amino arylcarbaldehydes; 2-Aminoquinolines; NITROGEN-HETEROCYCLES; ELECTRON-TRANSFER; N-HETEROCYCLES; QUINOLINE; PYRIDINE; SCAFFOLDS;
D O I
10.1002/slct.202204238
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(KOBu)-Bu-t mediates the reaction between 2-amino arylcarbaldehydes and benzyl/alkyl cyanides toward the expeditious formation of 2-aminoquinolines under transition-metal-free conditions. The described transformation proceeds through in-situ generated enimine intermediate from benzyl/alkyl cyanides under (KOBu)-Bu-t-mediated reaction conditions. The substituted 2-aminoquinolines were realized in excellent yields at room temperature and shorter reaction time. The designed process exhibits operational simplicity and broad functional group tolerance in delivering the products of high significance.
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页数:5
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