Selective synthesis of 3-methyleneindolin-2-ones by one-pot multicatalytic processes

被引:26
|
作者
Song, Ren-Jie [1 ]
Liu, Yu [1 ]
Li, Rong-Jiang [1 ]
Li, Jin-Heng [1 ]
机构
[1] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper; Palladium; Amination; C-H functionalization; Propiolamide; 3-Methyleneindolin-2-one; EFFICIENT COPPER CATALYST; GROWTH-FACTOR RECEPTOR; C-H FUNCTIONALIZATION; ARYL HALIDES; STEREOSELECTIVE-SYNTHESIS; DOMINO REACTIONS; TYROSINE KINASE; AMIDATION; TANDEM; DISCOVERY;
D O I
10.1016/j.tetlet.2009.04.066
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel one-pot multicatalytic route for the synthesis of 3-methyleneindolin-2-ones has been developed involving sequential copper-catalyzed amination and palladium-catalyzed C-H functionalization processes. In the presence of CuI and Pd(OAc)(2), a variety of propiolamides underwent the reaction with iodides to afford the corresponding 3-methyleneindolin-2-ones in moderate yields. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3912 / 3916
页数:5
相关论文
共 50 条
  • [1] Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols
    Casnati, Alessandra
    Lichosyt, Dawid
    Lainer, Bruno
    Veth, Lukas
    Dydio, Pawel
    ORGANIC LETTERS, 2021, 23 (09) : 3502 - 3506
  • [2] Cooperative Multicatalytic System for the One-Pot Synthesis of Octahydrospiro-β-carbolines
    Reddy, B. V. Subba
    Reddy, M. Rajashekhar
    Yarlagadda, Suresh
    Reddy, C. Ravikumar
    Kumar, G. Ravi
    Yadav, J. S.
    Sridhar, B.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8807 - 8814
  • [3] Synthesis of spiroquinolines through a one-pot multicatalytic and multicomponent cascade reaction
    Barluenga, Jose
    Mendoza, Abraham
    Rodriguez, Felix
    Fananas, Francisco J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) : 7044 - 7047
  • [4] ONE-POT SYNTHESIS OF SOME FUSED PYRAN-2-ONES
    KEPE, V
    KOCEVAR, M
    POLANC, S
    HETEROCYCLES, 1995, 41 (06) : 1299 - 1305
  • [5] One-Pot Multicatalytic Approaches for the Synthesis of Cyclohepta[b]indoles, Indolotropones, and Tetrahydrocarbazoles
    Mishra, Uttam K.
    Yadav, Sonu
    Ramasastry, S. S. V.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13): : 6729 - 6737
  • [6] Palladium-catalyzed cross-coupling reactions in one-pot multicatalytic processes
    Lebel, Helene
    Ladjel, Chehla
    Brethous, Lise
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) : 13321 - 13326
  • [7] One-pot synthesis of symmetrically disubstituted 3H-phenoxazin-3-ones by selective oxidative condensation with LTA
    Sridharan, Vellaisamy
    Dhanalakshmi, Pandi
    Muthusubramanian, Shanmugam
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (02) : 491 - 493
  • [8] Photoredox One-Pot Synthesis of 3,4-Dihydroquinolin-2(1 H )-ones
    He, Jing-Yao
    Bai, Qi-Fan
    Li, Xuewen
    Shou, Jianxin
    Feng, Gaofeng
    SYNLETT, 2022, 33 (07) : 679 - 683
  • [9] A new one-pot synthesis of 1-phenylpyrazolidin-3-ones. II
    Marton, GI
    Marton, AL
    REVISTA DE CHIMIE, 2004, 55 (07): : 555 - 557
  • [10] Selective "One-Pot" Synthesis of Functionalized Cyclopentenones
    Varea, Teresa
    Alcalde, Ana
    Lopez de Dicastillo, Carolina
    Ramirez de Arellano, Carmen
    Cossio, Fernando P.
    Asensio, Gregorio
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14): : 6327 - 6331