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
  • [1] Metal free synthesis of functionalized 1-aryl isoquinolines via iodine mediated oxidative dehydrogenation and ring opening of lactam in isoindoloisoquinolinones
    Kamsali Murali Mohan Achari
    Muthupandi Karthick
    Chinnasamy Ramaraj Ramanathan
    Journal of Chemical Sciences, 2017, 129 : 679 - 690
  • [2] Iodine-Catalyzed Metal-Free Oxidative Ring Opening of 1-Aryltetrahydro--carbolines: Facile Synthesis of C-2 Aroyl and Aryl Methanimino Indole Derivatives
    Chauhan, Jyoti
    Luthra, Tania
    Sen, Subhabrata
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (34) : 4776 - 4786
  • [3] Transition metal-free synthesis of 2-aryl quinazolines via alcohol dehydrogenation
    Hima, P.
    Vageesh, M.
    Tomasini, Michele
    Poater, Albert
    Dey, Raju
    MOLECULAR CATALYSIS, 2023, 542
  • [4] Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols
    Dahatonde, Dipak J.
    Ghosh, Aritra
    Batra, Sanjay
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (19) : 2746 - 2751
  • [5] Metal-Free Asymmetric Synthesis of Indanes through Chiral Hypervalent Iodine(III)-Mediated Ring Contraction
    Ahmad, Anees
    Silva, Luiz F., Jr.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05) : 2174 - 2181
  • [6] Molecular iodine mediated transition-metal-free oxidative dehydrogenation of 4,7-dihydropyrazolo[3,4-b]pyridines
    Aggarwal, Ranjana
    Singh, Gulshan
    Kumar, Suresh
    SYNTHETIC COMMUNICATIONS, 2021, 51 (23) : 3601 - 3609
  • [7] A mild and metal-free synthesis of 2-and 1-alkyl/aryl/dialkyl-aminoquinolines and isoquinolines
    Nanaji, Yerramsetti
    Kirar, Seema
    Pawar, Sandip, V
    Yadav, Ashok Kumar
    RSC ADVANCES, 2020, 10 (13) : 7628 - 7634
  • [8] Metal-Free Oxidative Coupling Reactions via σ-Iodonium Intermediates: The Efficient Synthesis of Bithiophenes Using Hypervalent Iodine Reagents
    Morimoto, Koji
    Nakae, Tomofumi
    Yamaoka, Nobutaka
    Dohi, Toshifumi
    Kita, Yasuyuki
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (31) : 6326 - 6334
  • [9] Metal-Free Synthesis of 4-Aryl-2-quinolone Derivatives by Iodine-Mediated Intramolecular C-H Amidation
    Ghosh, Subhankar
    Chattopadhyay, Shital K.
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (20) : 4727 - 4738
  • [10] Iodine Promoted One-Pot Synthesis of 2-Aryl Benzoxazoles from Amidoximes via Oxidative Cyclization and Ring Contraction
    Zhang, Yong
    Ji, Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (45) : 7506 - 7510