17104-70-0Relevant articles and documents
Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic N-Oxides
Zhang, Dong,Cai, Jinlin,Du, Jinze,Wang, Qingdong,Yang, Jinming,Geng, Rongqing,Fang, Zheng,Guo, Kai
supporting information, p. 1434 - 1438 (2022/03/01)
An efficient and green electrochemical N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method, sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of the difluoromethyl moiety, and various N-ortho-selective difluoromethylation quinoline and isoquinoline N-oxides were obtained in good to excellent yields under a constant current. In addition, the reaction was easy to scale up and maintained a good yield. Preliminary mechanism studies suggested that the reaction undergoes a free-radical addition and hydrogen elimination pathway.
Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions
Dhiman, Ankit Kumar,Thakur, Ankita,Kumar, Inder,Kumar, Rakesh,Sharma, Upendra
, p. 9244 - 9254 (2020/08/14)
A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.
Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions
Sarmah, Bikash Kumar,Konwar, Monuranjan,Bhattacharyya, Dipanjan,Adhikari, Priyanka,Das, Animesh
supporting information, p. 5616 - 5625 (2019/11/22)
A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).
