title: Arylative cyclization of 2-isocyanobiphenyls with anilines: one-pot synthesis of 6-arylphenanthridines via competitive reaction pathways.
abstract: 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.
authors.affiliation: State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , 190 Kaiyuan Avenue, Guangzhou 510530, China.
authors.forename: Zhonghua
authors.initials: Z
authors.lastname: Xia
authors.forename: Jinbo
authors.initials: J
authors.lastname: Huang
authors.forename: Yimiao
authors.initials: Y
authors.lastname: He
authors.forename: Jiaji
authors.initials: J
authors.lastname: Zhao
authors.forename: Jian
authors.initials: J
authors.lastname: Lei
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhu
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000814:Aniline Compounds; D001713:Biphenyl Compounds; D009570:Nitriles; D010617:Phenanthridines; C023650:aniline