Synthesis of isoquinolines via visible light-promoted insertion of vinyl isocyanides with diaryliodonium salts

被引:110
作者
Jiang, Heng [1 ]
Cheng, Yuanzheng [1 ]
Wang, Ruzhi [1 ]
Zhang, Yan [1 ]
Yu, Shouyun [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
PERIPHERAL BENZODIAZEPINE-RECEPTOR; MEDIATED ELECTROPHILIC CYCLIZATION; H BOND ACTIVATION; DE-NOVO SYNTHESIS; SUBSTITUTED ISOQUINOLINES; PHOTOREDOX CATALYSIS; PHENANTHRIDINE DERIVATIVES; INTERNAL ALKYNES; SULFONYLMETHYL ISOCYANIDES; REGIOSELECTIVE SYNTHESIS;
D O I
10.1039/c4cc01122h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A synthetic strategy for multi-substituted isoquinoline derivatives has been developed using visible light-promoted vinyl isocyanide insertion with diaryliodonium salts at room temperature. The methodology presented here represents the first example of isoquinoline synthesis via somophilic isocyanide insertion.
引用
收藏
页码:6164 / 6167
页数:4
相关论文
共 56 条
  • [1] Mapping and fitting the peripheral benzodiazepine receptor binding site by carboxamide derivatives. Comparison of different approaches to quantitative ligand-receptor interaction modeling
    Anzini, M
    Cappelli, A
    Vomero, S
    Seeber, M
    Menziani, MC
    Langer, T
    Hagen, B
    Manzoni, C
    Bourguignon, JJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (08) : 1134 - 1150
  • [2] On the synthesis of vinyl isonitriles
    Baldwin, JE
    Chen, DQ
    Russell, AT
    [J]. CHEMICAL COMMUNICATIONS, 1997, (24) : 2389 - 2390
  • [3] Bentley K. W., 1998, The Isoquinoline Alkaloids, V1
  • [4] Synthesis using aromatic homolytic substitution - recent advances
    Bowman, W. Russell
    Storey, John M. D.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (11) : 1803 - 1822
  • [5] Mapping the peripheral benzodiazepine receptor binding site by conformationally restrained derivatives of 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide (PK11195)
    Cappelli, A
    Anzini, M
    Vomero, S
    DeBenedetti, PG
    Menziani, MC
    Giorgi, G
    Manzoni, C
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (18) : 2910 - 2921
  • [6] Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives
    Cheng, Yuanzheng
    Jiang, Heng
    Zhang, Yan
    Yu, Shouyun
    [J]. ORGANIC LETTERS, 2013, 15 (21) : 5520 - 5523
  • [7] A Pd(II)-Catalyzed Ring-Expansion Reaction of Cyclic 2-Azidoalcohol Derivatives: Synthesis of Azaheterocycles
    Chiba, Shunsuke
    Xu, Yan-Jun
    Wang, Yi-Feng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) : 12886 - +
  • [8] Ruthenium-Catalyzed Highly Regioselective Cyclization of Ketoximes with Alkynes by C-H Bond Activation: A Practical Route to Synthesize Substituted Isoquinolines
    Chinnagolla, Ravi Kiran
    Pimparkar, Sandeep
    Jeganmohan, Masilamani
    [J]. ORGANIC LETTERS, 2012, 14 (12) : 3032 - 3035
  • [9] Dömling A, 2005, SYNTHESIS-STUTTGART, P662
  • [10] Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones
    Donohoe, Timothy J.
    Pilgrim, Ben S.
    Jones, Geraint R.
    Bassuto, Jose A.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (29) : 11605 - 11608