A novel approach to 2-arylated quinolines: Electrocyclization of alkynyl imines via vinylidene complexes

被引:111
|
作者
Sangu, K [1 ]
Fuchibe, K [1 ]
Akiyama, T [1 ]
机构
[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
关键词
D O I
10.1021/ol036190a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkynyl imines underwent [4 + 2] electrocyclization in the presence of 20 mol % W(CO)(5)(THF) to give 2-arylated quinolines in good yields. A deuterium labeling study suggests that the reaction proceeds via a tungsten vinylidene complex.
引用
收藏
页码:353 / 355
页数:3
相关论文
共 50 条
  • [21] Novel approach to synthesis of [c]-condensed decahydroisoindolo[2,1-a]quinolines
    Zubkov F.I.
    Zaytsev V.P.
    Nikitina E.V.
    Mikhaylova N.M.
    Aleksandrov G.G.
    Borisov R.S.
    Varlamov A.V.
    Chemistry of Heterocyclic Compounds, 2005, 41 (2) : 273 - 274
  • [22] Novel synthetic approach to [c]-fused decahydroisoindolo[2,1-a]quinolines
    Zubkov, FI
    Zaytsev, VP
    Nikitina, EV
    Mikhaylova, NM
    Alexandrov, GG
    Borisov, RS
    Varlamov, AV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2005, (02): : 303 - 304
  • [23] Accessing indole-isoindole derivatives via palladium-catalyzed [3+2] cyclization of isocyanides with alkynyl imines
    Chen, Dianpeng
    Li, Jianming
    Liu, Gongle
    Zhang, Xiuhua
    Wang, Xin
    Liu, Yongwei
    Liu, Xuan
    Liu, Xinghai
    Li, Yongqin
    Shan, Yingying
    CHEMICAL COMMUNICATIONS, 2023, 59 (70) : 10540 - 10543
  • [24] A novel strategy for the synthesis of 2,6-diaryl-1,2-dihydropyridines via 6π-electrocyclization
    Vincze, Zoltan
    Nemes, Peter
    TETRAHEDRON, 2013, 69 (30) : 6269 - 6274
  • [25] Exploring the capabilities of 2-alkynyl aryl/benzyl azides: synthesis approaches for indoles, quinolines, and their derivatives via transition metal catalysis
    Hosseininezhad, Seyedmohammad
    Abad, Sina Pirani Ahmad
    Ramazani, Ali
    RSC ADVANCES, 2025, 15 (02) : 1163 - 1204
  • [26] Coordination and coupling of OH-functionalized C-2 units at a single metal center: The synthesis of alkynyl(vinylidene), alkynyl(enyne), bis(alkynyl)hydrido, enynyl, and hexapentaene rhodium complexes from propargylic alcohols as precursors
    Werner, H
    Wiedemann, R
    Mahr, N
    Steinert, P
    Wolf, J
    CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (05) : 561 - 569
  • [27] Facile synthesis of 2-substituted quinolines and 3-alkynyl-2-aryl-2H-Indazole via SnCl2-mediated reductive cyclization
    Sudhapriya, Narayanasamy
    Nandakumar, Avanashiappan
    Perumal, Paramasivan Thirumalai
    RSC ADVANCES, 2014, 4 (102) : 58476 - 58480
  • [28] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .69. 2-(ACYLAMINO)ETHENYL KETENE IMINES FROM [2-(ACYLAMINO)ETHENYL]CARBENE COMPLEXES AND THEIR RING-CLOSING METATHESIS TO PYRROLES OR ELECTROCYCLIZATION TO 1,4-DIAMINONAPHTHALENES
    AUMANN, R
    JASPER, B
    GODDARD, R
    KRUGER, C
    CHEMISCHE BERICHTE, 1994, 127 (04) : 717 - 724
  • [29] NOVEL ALLENYLIDENE ALKYNYL AND AMMONIA ALKYNYL METAL-COMPLEXES VIA SELECTIVE SYNTHESIS OF MONO AND BIS ALKYNYL RUTHENIUM(II) COMPLEXES - CRYSTAL-STRUCTURE OF TRANS-[RU(NH3)(C-EQUIVALENT-TO-CPH)(PH2PCH2CH2PPH2)2]PF6
    TOUCHARD, D
    MORICE, C
    CADIERNO, V
    HAQUETTE, P
    TOUPET, L
    DIXNEUF, PH
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) : 859 - 860
  • [30] Novel Heterometallic Fe-Ru2-Fe Arrays via "Complex of Complexes" Approach
    Wang, Cai-Feng
    Zuo, Jing Lin
    Ying, Jie-Wen
    Ren, Tong
    You, Xiao-Zeng
    INORGANIC CHEMISTRY, 2008, 47 (20) : 9716 - 9722