Synthesis of β- and γ-Carbolinones via Pd-Catalyzed Direct Dehydrogenative Annulation (DDA) of Indole-carboxamides with Alkynes Using Air as the Oxidant

被引:131
作者
Shi, Zhuangzhi [1 ]
Cui, Yuxin [1 ]
Jiao, Ning [1 ,2 ]
机构
[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100083, Peoples R China
[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
基金
美国国家科学基金会;
关键词
C-H ACTIVATION; BOND FUNCTIONALIZATION; INTERNAL ALKYNES; OXIDATIVE CYCLIZATION; AROMATIC SUBSTITUTION; DERIVATIVES; PALLADIUM(II); ARYLATION; MULTIPLE; ANILINES;
D O I
10.1021/ol1007839
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed direct dehydrogenative annulation (DDA) of indolecarboxamides with internal alkynes via C-H and N-H bond cleavage using air as the oxidant was developed. With this method, both beta- and gamma-carbolinones can be easily prepared under the mild conditions.
引用
收藏
页码:2908 / 2911
页数:4
相关论文
共 53 条
  • [1] Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones
    Beccalli, EM
    Broggini, G
    Marchesini, A
    Rossi, E
    [J]. TETRAHEDRON, 2002, 58 (33) : 6673 - 6678
  • [2] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles
    Beck, EM
    Grimster, NP
    Hatley, R
    Gaunt, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) : 2528 - 2529
  • [3] Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway
    Chernyak, Natalia
    Gevorgyan, Vladimir
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) : 5636 - +
  • [4] CINCINELLI R, 2008, SYNTHESIS-STUTTGART, P1517
  • [5] 2-(QUINUCLIDIN-3-YL)PYRIDO[4,3-B]INDOL-1-ONES AND ISOQUINOLIN-1-ONES - POTENT CONFORMATIONALLY RESTRICTED 5-HT(3) RECEPTOR ANTAGONISTS
    CLARK, RD
    MILLER, AB
    BERGER, J
    REPKE, DB
    WEINHARDT, KK
    KOWALCZYK, BA
    EGLEN, RM
    BONHAUS, DW
    LEE, CH
    MICHEL, AD
    SMITH, WL
    WONG, EHF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (18) : 2645 - 2657
  • [6] Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C-H Bond Cleavage Using Dioxygen as Oxidant
    Ding, Shengtao
    Shi, Zhuangzhi
    Jiao, Ning
    [J]. ORGANIC LETTERS, 2010, 12 (07) : 1540 - 1543
  • [7] C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls
    Dwight, Timothy A.
    Rue, Nicholas R.
    Charyk, Dagmara
    Josselyn, Ryan
    DeBoef, Brenton
    [J]. ORGANIC LETTERS, 2007, 9 (16) : 3137 - 3139
  • [8] Palladium-catalyzed intramolecular arylation reaction:: Mechanism and application for the synthesis of polyarenes
    Echavarren, AM
    Gómez-Lor, B
    González, JJ
    de Frutos, O
    [J]. SYNLETT, 2003, (05) : 585 - 597
  • [9] Gold-catalyzed cycloisomerization of N-propargylindole-2-carboxamides:: Application toward the synthesis of lavendamycin analogues
    England, Dylan B.
    Padwa, Albert
    [J]. ORGANIC LETTERS, 2008, 10 (16) : 3631 - 3634
  • [10] Lewis acid-directed cyclocondensation of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:: A new regioselective synthesis of oxygenated carbolines
    Engler, TA
    Wanner, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) : 2444 - 2457