Manganese(ii)-catalysed dehydrogenative annulation involving C-C bond formation: highly regioselective synthesis of quinolines

被引:13
|
作者
Wang, Chengniu [1 ]
Yang, Jinfei [1 ]
Meng, Xiao [1 ]
Sun, Yufeng [1 ]
Man, Xuyan [1 ]
Li, Jinxia [1 ]
Sun, Fei [1 ]
机构
[1] Nantong Univ, Inst Reprod Med, Med Sch, Nantong 226019, Peoples R China
基金
中国国家自然科学基金;
关键词
H ACTIVATION; CATALYZED ARYLATION; COPPER; FUNCTIONALIZATION; PALLADIUM; ALKYNES; ALKENYLATION; ALKYLATIONS; SELECTIVITY; INSERTION;
D O I
10.1039/c9dt00647h
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An inexpensive nontoxic manganese(ii)-catalysed dehydrogenative annulation was developed for C-C bond formation. The reaction showed high selectivity and efficiency across a broad substrate scope. Remarkably simple conditions and the ability to conduct gram-scale synthesis underscore this method's utility. To demonstrate the potential of this approach, we tested the drug effects of compound 3n, which showed activity for blocking vascular development. The results of this study will be important for the treatment of eye diseases and tumors caused by vascular proliferation.
引用
收藏
页码:4474 / 4478
页数:5
相关论文
共 50 条
  • [41] Participation of (η3-allyl)ruthenium(II) complexes in C-C bond formation and C-C bond cleavage.: A theoretical study
    Sakaki, S
    Ohki, T
    Takayama, T
    Sugimoto, M
    Kondo, T
    Mitsudo, T
    ORGANOMETALLICS, 2001, 20 (14) : 3145 - 3158
  • [42] Carbofluorination of π-Bonds and Related Reactions Involving Tandem C-C/C-F Bond Formation
    McKnight, E. Ali
    Cadwallader, Dusty
    Le, Christine M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (19)
  • [43] Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters
    Chen, Pu
    Huang, Huawen
    Tan, Qi
    Ji, Xiaochen
    Zhao, Feng
    MOLECULES, 2023, 28 (06):
  • [44] Synthesis of C-glycosides via intramolecular C-C bond formation.
    Gregory, GS
    Kraynack, EA
    Mayhugh, DR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U183 - U183
  • [45] Biocatalytic Oxidative C-C Bond Formation Catalysed by the Berberine Bridge Enzyme: Optimal Reaction Conditions
    Resch, Verena
    Schrittwieser, Joerg H.
    Wallner, Silvia
    Macheroux, Peter
    Kroutil, Wolfgang
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (13) : 2377 - 2383
  • [46] The mechanism of C-C bond formation on the Pt(IV) center involving chelate metallocycle ligands
    Ananikov, VP
    Mitchenko, SA
    Beletskaya, IP
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 604 (02) : 290 - 295
  • [47] Synthesis of Diversely Substituted Indoloquinolinones via Pd(II)/Cu(II)-Mediated Oxidative C-C Bond Formation and I(III)-Mediated C-N Bond Formation
    Zhang, Xiang
    Zhang-Negrerie, Daisy
    Deng, Jun
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (24): : 12750 - 12759
  • [48] Mechanistic aspects of C-C bond formation involving allylpalladium complexes:: the role of computational studies
    Cárdenas, DJ
    Echavarren, AM
    NEW JOURNAL OF CHEMISTRY, 2004, 28 (03) : 338 - 347
  • [49] Regioselective functionalization of iminophosphoranes through Pd-mediated C-H bond activation: C-C and C-X bond formation
    Aguilar, David
    Navarro, Rafael
    Soler, Tatiana
    Urriolabeitia, Esteban P.
    DALTON TRANSACTIONS, 2010, 39 (43) : 10422 - 10431
  • [50] InIII-Catalysed Tandem C-C and C-O Bond Formation between Phenols and Allylic Acetates
    Vece, Vito
    Ricci, Jeremy
    Poulain-Martini, Sophie
    Nava, Paola
    Carissan, Yannick
    Humbel, Stephane
    Dunach, Elisabet
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (32) : 6239 - 6248