Palladium(0)-Catalyzed Heck Reaction/C-H Activation/Amination Sequence with Diaziridinone: A Facile Approach to Indolines

被引:125
作者
Zheng, Huaiji [1 ]
Zhu, Yingguang [1 ]
Shi, Yian [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
基金
美国国家卫生研究院;
关键词
CH activation; cyclization; heterocycles; palladium; synthetic methods; BOND FORMATION; PD(0)-CATALYZED DIAMINATION; PD(II)-CATALYZED AMINATION; CONJUGATED DIENES; TERMINAL OLEFINS; ARYL HALIDES; PALLADIUM; FUNCTIONALIZATION; DERIVATIVES; C(SP(3))-H;
D O I
10.1002/anie.201405365
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Indolines are important moieties present in various biologically significant molecules and have attracted considerable attention in synthetic chemistry. This paper describes a Heck reaction/CH activation/amination sequence for forming indolines using di-tert-butyldiaziridinone. The reaction process likely proceeds via a pallada(II)cycle, which is converted into an indoline by oxidative addition to the diaziridinone and two subsequent CN bond formations.
引用
收藏
页码:11280 / 11284
页数:5
相关论文
共 83 条
  • [1] Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents
    Abdel-Rahman, AH
    Keshk, EM
    Hanna, MA
    El-Bady, SM
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) : 2483 - 2488
  • [2] Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
  • [3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [4] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [5] Routes toward enantiopure 2-substituted indolines: an overview
    Anas, Saithalavi
    Kagan, Henri B.
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (19) : 2193 - 2199
  • [6] Discovery of cis-N-(1-(4-(Methylamino)cyclohexyl)indolin-6-yl)thiophene-2-carboximidamide: A 1,6-Disubstituted Indoline Derivative as a Highly Selective Inhibitor of Human Neuronal Nitric Oxide Synthase (nNOS) without Any Cardiovascular Liabilities
    Annedi, Subhash C.
    Ramnauth, Jailall
    Maddaford, Shawn P.
    Renton, Paul
    Rakhit, Suman
    Mladenova, Gabriela
    Dove, Peter
    Silverman, Sarah
    Andrews, John S.
    Felice, Milena D.
    Porreca, Frank
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (02) : 943 - 955
  • [7] Indoline derivatives as 5-HT2C receptor agonists
    Bentley, JM
    Adams, DR
    Bebbington, D
    Benwell, KR
    Bickerdike, MJ
    Davidson, JEP
    Dawson, CE
    Dourish, CT
    Duncton, MAJ
    Gaur, S
    George, AR
    Giles, PR
    Hamlyn, RJ
    Kennett, GA
    Knight, AR
    Malcolm, CS
    Mansell, HL
    Misra, A
    Monck, NJT
    Pratt, RM
    Quirk, K
    Roffey, JRA
    Vickers, SP
    Cliffe, IA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) : 2367 - 2370
  • [8] 5-HYDROXYTRYPTAMINE (5-HT3) RECEPTOR ANTAGONISTS .2. 1-INDOLINECARBOXAMIDES
    BERMUDEZ, J
    DABBS, S
    JOINER, KA
    KING, FD
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (07) : 1929 - 1932
  • [9] Catellani, 1997, ANGEW CHEM, V109, P142
  • [10] Catalytic multistep reactions via palladacycles
    Catellani, M
    [J]. SYNLETT, 2003, (03) : 298 - 313