Metal-Free Synthesis 6-Benzylphenanthridines via Radical Addition/Cyclization of 2-Isocyanobiphenyls

被引：7
|
作者：
Lu, Yuling [1 ]
Chen, Li [1 ]
Chen, Xia [1 ]
Yao, Meng [1 ]
Luo, Zengwei [1 ]
Zhang, Yonghui [1 ]
机构：
[1] Huazhong Univ Sci & Technol, Hubei Key Lab Nat Med Chem & Resource Evaluat, Sch Pharm, Tongji Med Coll, Wuhan 430030, Hubei, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 02期
基金：
中国国家自然科学基金;
关键词：
phenanthridine; metal-free; radical; isocyanobiphenyl; toluene; ONE-POT SYNTHESIS; OXIDATIVE CYCLIZATION; TOLUENE DERIVATIVES; PHENANTHRIDINES; INSERTION/CYCLIZATION; FUNCTIONALIZATION; DECARBOXYLATION; ISOQUINOLINES; ISOCYANIDES; ISONITRILES;
D O I：
10.1055/s-0039-1690218
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and practical approach has been established for the synthesis of 6-benzylphenanthridines from benzylic hydrocarbons and 2-isocyanobiphenyls via C(sp(3))-H/C(sp(2))-H bond functionalization under metal-free condition. The reaction exhibits good functional group tolerance and delivers the target products in moderate to excellent yields. The preliminary mechanistic investigation revealed that a radical intermediate might be involved in this reaction.
引用
收藏
页码：290 / 296
页数：7
相关论文
共 50 条
  • [1] Synthesis of 6-Trichloromethylphenanthridines by Transition Metal-Free Radical Cyclization of 2-Isocyanobiphenyls
    Zhou, Yuhan
    Wu, Changpeng
    Dong, Xiaoliang
    Qu, Jingping
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (12): : 5202 - 5208
  • [2] Metal-free radical oxidative decarboxylation/cyclization of acyl peroxides and 2-isocyanobiphenyls
    Pan, Changduo
    Zhang, Honglin
    Han, Jie
    Cheng, Yixiang
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2015, 51 (18) : 3786 - 3788
  • [3] Synthesis of 6-substituted phenanthridines by metal-free, visible-light induced aerobic oxidative cyclization of 2-isocyanobiphenyls with hydrazines
    Xiao, Tiebo
    Li, Linyong
    Lin, Guoliang
    Wang, Qile
    Zhang, Ping
    Mao, Zong-wan
    Zhou, Lei
    GREEN CHEMISTRY, 2014, 16 (05) : 2418 - 2421
  • [4] Synthesis of 6-(arylthio)phenanthridines by cyclization reaction of 2-isocyanobiphenyls with thiols
    Wu, Changpeng
    Zhou, Yuhan
    Dong, Xiaoliang
    Qu, Jingping
    ARKIVOC, 2016, : 110 - 124
  • [5] Direct synthesis of 6-sulfonylated phenanthridines via silver-catalyzed radical sulfonylation-cyclization of 2-isocyanobiphenyls
    Singh, Manjula
    Yadav, Arvind K.
    Yadav, Lal Dhar S.
    Singh, Rana Krishna Pal
    TETRAHEDRON LETTERS, 2018, 59 (33) : 3198 - 3201
  • [6] Recent Advancements in Synthesis of Phenanthridines via 2-Isocyanobiphenyls
    Dey, Ashutosh
    Kumar, Vikash
    Chatterjee, Rana
    Behera, Ananya
    Maurya, Rohit Kumar
    Burra, Amarender Goud
    Kumar, Shubham
    Khatravath, Mahender
    Dandella, Rambabu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (11)
  • [7] PhI(OAc)2-Mediated Synthesis of 6-(Trifluoromethyl)phenanthridines by Oxidative Cyclization of 2-Isocyanobiphenyls with CF3SiMe3 under Metal-Free Conditions
    Wang, Qile
    Dong, Xichang
    Xiao, Tiebo
    Zhou, Lei
    ORGANIC LETTERS, 2013, 15 (18) : 4846 - 4849
  • [8] Preparation of 6-Difluoromethylphosphonated Phenanthridines by Visible-Light-Driven Radical Cyclization of 2-Isocyanobiphenyls
    Wang, Shuang
    Jia, Wen-Liang
    Wang, Lin
    Liu, Qiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (31) : 6817 - 6821
  • [9] Synthesis of 6-aroyl phenanthridines by Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls with benzylic alcohols
    Nie, Ziyi
    Ding, Qiuping
    Peng, Yiyuan
    TETRAHEDRON, 2016, 72 (50) : 8350 - 8357
  • [10] 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
    ORGANIC LETTERS, 2014, 16 (09) : 2546 - 2549
12345