Metal free synthesis of functionalized 1-aryl isoquinolines via iodine mediated oxidative dehydrogenation and ring opening of lactam in isoindoloisoquinolinones

被引:5
作者
Achari, Kamsali Murali Mohan [1 ]
Karthick, Muthupandi [1 ]
Ramanathan, Chinnasamy Ramaraj [1 ]
机构
[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
关键词
Iodine; oxidative dehydrogenation; oxoisoaporphines; 1-Azabenzanthrone; isoindoloisoquinolinones; MENISPERMUM-DAURICUM DC; OXOISOAPORPHINE ALKALOIDS; DERIVATIVES; INHIBITORS; MENISPORPHINE; LAKSHMININE; ACTIVATION; DNA;
D O I
10.1007/s12039-017-1301-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile and convenient method for the synthesis of substituted 2-(isoquinolin-1-yl)benzoic acids from isoindoloisoquinolinones in the presence of molecular iodine under sealed tube condition at 100 has been developed. This methodology involves the oxidative dehydrogenation and ring opening of hydroxy lactam/methoxy lactam to furnish the 2-(isoquinolin-1-yl)benzoic acids. Some of these acids are successfully cyclized to furnish the azabenzanthrone derivatives, the potential precursors for the synthesis of menisporphine alkaloids and daurioxoisoaporphines.
引用
收藏
页码:679 / 690
页数:12
相关论文
共 50 条
  • [21] Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C-C and C-N bonds
    Yan, Kelu
    Yang, Daoshan
    Wei, Wei
    Li, Guoqing
    Sun, Mingyang
    Zhang, Qingyun
    Tian, Laijin
    Wang, Hua
    RSC ADVANCES, 2015, 5 (121): : 100102 - 100105
  • [22] Modular synthesis of (E)-cinnamaldehydes directly from allylarenes via a metal-free DDQ-mediated oxidative process
    Xu, Ting-Ting
    Jiang, Tao-Shan
    Han, Xiao-Lan
    Xu, Yuan-Hong
    Qiao, Jin-Ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (29) : 5350 - 5358
  • [23] Metal-Free, One-Pot Oxidative Triple Functionalization of Azaarenes with Methyl Arenes Mediated by Molecular Iodine/TBHP: Synthesis of N-Benzylated Iodo(iso)quinolinones
    Shantharjun, Bangarigalla
    Rajeswari, Radhakrishnan
    Vani, Damera
    Unnava, Ramanjaneyulu
    Sridhar, Balasubramanian
    Reddy, Kallu Rajender
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (11) : 2162 - 2171
  • [24] CuBr-mediated synthesis of 1,4-naphthoquinones via ring expansion of 2-aryl-1,3-indandiones
    Zhang, Xu
    Wang, Di
    Chang, Mengfan
    Wang, Wanya
    Shen, Zhi
    Xu, Xuefeng
    CHEMICAL COMMUNICATIONS, 2023, 59 (82) : 12326 - 12329
  • [25] Oxidative Aromatic C-O Bond Formation: Synthesis of 3-Functionalized Benzo[b]furans by FeCl3-Mediated Ring Closure of α-Aryl Ketones
    Liang, Zhidan
    Hou, Weizhe
    Du, Yunfei
    Zhang, Yongliang
    Pan, Yan
    Mao, Deng
    Zhao, Kang
    ORGANIC LETTERS, 2009, 11 (21) : 4978 - 4981
  • [26] Cascade Reactions: Catalytic Synthesis of Functionalized 1,3-Dihydroisobenzofuran and Tetrahydrofuran Derivatives by Sequential Nucleophilic Ring Opening-Heterocyclization-Oxidative Carbonylation of Alkynyloxiranes
    Della Ca', Nicola
    Campanini, Fabio
    Gabriele, Bartolo
    Salerno, Giuseppe
    Massera, Chiara
    Costa, Mirco
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) : 2423 - 2432
  • [27] Visible light-mediated ring opening and cyclization of aryl cyclopropanes: efficient synthesis of pyrrolo[1,2-a]quinoxalin-4(5H)-ones with antineoplastic activity
    Shen, Jiabin
    Yang, Yong
    Chen, Chao
    Xu, Hao
    Shen, Chao
    Zhang, Pengfei
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (06) : 1758 - 1764
  • [28] Metal-Free Nitrogen- and Boron-Codoped Mesoporous Carbons for Primary Amides Synthesis from Primary Alcohols via Direct Oxidative Dehydrogenation
    Shang, Sensen
    Chen, Pei-Pei
    Wang, Lianyue
    Lv, Ying
    Li, Wei-Xue
    Gao, Shuang
    ACS CATALYSIS, 2018, 8 (11): : 9936 - 9944
  • [29] Electrochemical Synthesis of 2-Aryl-3-(2-aminoaryl)quinoxalines via Oxidative Dearomatization/Ring-Opening/Cyclization Cascade Sequence of 2-Arylindoles with 1,2-Diaminoarenes
    Nagare, Yadav Kacharu
    Yadav, Jyothi
    Dolas, Atul Jankiram
    Shah, Imtiyaz Ahmad
    Rangan, Krishnan
    Choudhary, Rahul
    Iype, Eldhose
    Kumar, Indresh
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15) : 11111 - 11121
  • [30] Indoles Oxidative Ring-Opening/Cyclization Cascade with the 1,2-Diaminoarenes: Direct Synthesis of 2-Aryl-3-(2-aminoaryl)quinoxalines
    Yan, Jianwei
    Zheng, Linxia
    Wang, Jiangfei
    Liu, Xiaomin
    Hu, Youhong
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) : 6347 - 6351