Transition-Metal Free Construction of Isoquinoline-fused Triazines Containing Alkenyl C-X Bonds

被引:51
作者
Cheng, Xiao [1 ,2 ]
Cao, Xia [1 ,2 ]
Zhou, Shuang-Jing [1 ,2 ]
Cai, Bao-Gui [1 ,2 ]
He, Xiang-Kui [1 ,2 ]
Xuan, Jun [1 ,2 ,3 ]
机构
[1] Anhui Univ, Dept Chem, Hefei 230601, Anhui, Peoples R China
[2] Anhui Univ, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Func, Hefei 230601, Anhui, Peoples R China
[3] Anhui Univ, Inst Phys Sci & Informat Technol, Hefei 230601, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
Transition-metal free; Isoquinoline-fused Triazines'; azaoxyallyl cations; C; N-cyclic azomethine imines; heterocyclic compounds; C; N-CYCLIC AZOMETHINE IMINES; FORMED AZAOXYALLYL CATIONS; AZA-OXYALLYL CATIONS; 3+3 CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; ACCESS; CYCLIZATION; ANNULATION; CHEMISTRY; HETEROCYCLES;
D O I
10.1002/adsc.201801181
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A halogen and base-mediated [3+3]-cycloaddition reaction of in situ generated azaoxyallyl cations with in situ formed C,N-cyclic azomethine imines is reported. This one-pot transition metal-free cycloaddition process exhibits broad substrate scope, excellent functional group tolerance, and affords a series of biologically important isoquinoline-fused triazines in good to excellent yields, which containing valuable alkenyl C-X bonds (X-Br, I).
引用
收藏
页码:1230 / 1235
页数:6
相关论文
共 68 条
  • [1] Access to 4-Oxazolidinones: A (3+2) Cycloaddition Approach
    Acharya, Arjun
    Montes, Karissa
    Jeffrey, Christopher S.
    [J]. ORGANIC LETTERS, 2016, 18 (23) : 6082 - 6085
  • [2] Dearomative Indole Cycloaddition Reactions of Aza-Oxyallyl Cationic Intermediates: Modular Access to Pyrroloindolines
    Acharya, Arjun
    Anumandla, Devendar
    Jeffrey, Christopher S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (47) : 14858 - 14860
  • [3] Intramolecular Aza-[4+3] Cycloaddition Reactions of α-Halohydroxamates
    Acharya, Arjun
    Eickhoff, John A.
    Jeffrey, Christopher S.
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (13): : 1825 - 1836
  • [4] Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides
    Adrio, Javier
    Carretero, Juan C.
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (24) : 6784 - 6794
  • [5] Exploiting [2+2] cycloaddition chemistry: achievements with allenes
    Alcaide, Benito
    Almendros, Pedro
    Aragoncillo, Cristina
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) : 783 - 816
  • [6] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
  • [7] Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations
    An, Yuanyuan
    Xia, Hongguang
    Wu, Jie
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (68) : 10415 - 10418
  • [8] Trapping the elusive aza-oxyallylic cation: new opportunities in heterocycloaddition chemistry
    Barnes, Korry L.
    Koster, Anna K.
    Jeffrey, Christopher S.
    [J]. TETRAHEDRON LETTERS, 2014, 55 (34) : 4690 - 4696
  • [9] Seven-membered rings by cyclization at transition metals:: [4+3], [3+2+2], [5+2]
    Butenschoen, Holger
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (29) : 5287 - 5290
  • [10] Arylsulfonyl Radical Triggered 1,6-Enyne Cyclization: Synthesis of γ-Lactams Containing Alkenyl C-X Bonds
    Cao, Xia
    Cheng, Xiao
    Xuan, Jun
    [J]. ORGANIC LETTERS, 2018, 20 (02) : 449 - 452