1428265-01-3Relevant academic research and scientific papers
Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines
Malviya, Bhanwar Kumar,Singh, Karandeep,Jaiswal, Pradeep K.,Karnatak, Manvika,Verma, Ved Prakash,Badsara, Satpal Singh,Sharma, Siddharth
, p. 6367 - 6378 (2021/04/16)
Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.
Iron-Catalyzed Aerobic Dehydrogenative Kinetic Resolution of Cyclic Secondary Amines
Lu, Ran,Cao, Liya,Guan, Honghao,Liu, Lei
, p. 6318 - 6324 (2019/05/09)
A nonenzymatic iron-catalyzed dehydrogenative kinetic resolution of cyclic secondary amines using air as an oxidant has been reported. The economical and practical method is applicable to a series of cyclic benzylic amines, including 5,6-dihydrophenanthridines and 1,2-dihydroquinolines, with diverse functional groups at the α position in high yields with excellent enantioselectivities. The direct dehydrogenative kinetic resolution of advanced intermediates of bioactive molecules that are difficult to access using existing catalytic asymmetric synthetic strategy was also demonstrated.
Arylative cyclization of 2-isocyanobiphenyls with anilines: One-pot synthesis of 6-arylphenanthridines via competitive reaction pathways
Xia, Zhonghua,Huang, Jinbo,He, Yimiao,Zhao, Jiaji,Lei, Jian,Zhu, Qiang
, p. 2546 - 2549 (2014/05/20)
A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.
Modular synthesis of phenanthridine derivatives by oxidative cyclization of 2-isocyanobiphenyls with organoboron reagents
Tobisu, Mamoru,Koh, Keika,Furukawa, Takayuki,Chatani, Naoto
, p. 11363 - 11366 (2013/01/15)
Where HAS you been? A manganese-mediated annulation of 2-isocyanobiaryls with organoboronic acids is developed for the synthesis of a broad range of phenanthridine derivatives (see scheme). Mechanistic studies indicate that the reaction proceeds by the intramolecular homolytic aromatic substitution (HAS) of an imidoyl radical intermediate. Copyright
