Synthesis of 1,6-dihydropyrrolo[2,3-g]indazoles using Larock indole annulation

被引：20
|
作者：
Gavara, Laurent [1 ,2 ]
Anizon, Fabrice [1 ,2 ]
Moreau, Pascale [1 ,2 ]
机构：
[1] Univ Clermont Ferrand, Clermont Univ, Lab SEESIB, F-63000 Clermont Ferrand, France
[2] CNRS, UMR 6504, SEESIB, F-63177 Aubiere, France
来源：
TETRAHEDRON | 2011年 / 67卷 / 38期
关键词：
Indazole; Larock indole annulation; Pyrroloindazole; Regioselectivity; PALLADIUM-CATALYZED ANNULATION; 2,3-DISUBSTITUTED INDOLES; INTERNAL ALKYNES; INDAZOLE DERIVATIVES; N-IODOSUCCINIMIDE; HYDROGEN-PEROXIDE; ONE-POT; IODINATION; SONOGASHIRA; HETEROANNULATION;
D O I：
10.1016/j.tet.2011.07.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of 1,6-dihydropyrrolo[2,3-g]indazole derivatives is described. The indolic ring system is constructed via a Larock palladium-catalyzed annulation using terminal and internal alkynes. Additionally, when using internal alkynes for this reaction, we found that a directing effect on regioselectivity was mediated by the ester group of alkyl 3-substituted propiolate derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7330 / 7335
页数：6
相关论文
共 50 条
  • [31] [1,4]BENZODIOXINO[2,3-G]ISOQUINOLINES AND [1,4]DIOXINODIISOQUINOLINES
    BROWNE, EJ
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (08) : 1803 - 1811
  • [32] Facile and diverse synthesis of indolyl substituted 4,5,6,7-tetrahydro-4H-indol-4-ones and 1,6-dihydropyrrolo[2,3-c]pyrazol via multi-component reactions
    Wang, Jing
    Yu, Lu
    Jiang, Haoqiang
    Zhu, Songlei
    TETRAHEDRON LETTERS, 2025, 155
  • [33] SYNTHESIS OF THIA-ELLIPTICINE 5,11-DIMETHYLBENZOTHIENO[2,3-G]ISOQUINOLINE
    FUJIWARA, AN
    ACTON, EM
    GOODMAN, L
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (06) : 853 - &
  • [34] SYNTHESIS OF 1-FUNCTIONALIZED 5-METHYLNAPHTHO[2,3-G]ISOQUINOLINE-6,11-QUINONES
    CROISYDELCEY, M
    RAUTUREAU, M
    HUEL, C
    BISAGNI, E
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22): : 5301 - 5304
  • [35] Synthesis of Pyrrolo[2,3-b]indole via Iodine(III)-Mediated Intramolecular Annulation
    Tu, Dandan
    Ma, Liying
    Tong, Xiaogang
    Deng, Xu
    Xia, Chengfeng
    ORGANIC LETTERS, 2012, 14 (18) : 4830 - 4833
  • [36] SYNTHESIS OF LY288601, A 5,6-DIHYDROPYRROLO[2,3-D]PYRIMIDINE BASED ANTIFOLATE COMPOUND RELATED TO LY231514
    BARNETT, CJ
    WILSON, TM
    HETEROCYCLES, 1993, 35 (02) : 925 - 936
  • [37] SYNTHESIS OF 1-FUNCTIONALIZED-6-HYDROXY-4-METHYLNAPHTHO[2,3-G]ISOQUINOLINE-5,12-QUINONES AND 1-FUNCTIONALIZED-6,11-DIHYDROXY-4-METHYLNAPHTHO[2,3-G]ISOQUINOLINE-5,12-QUINONES
    CROISYDELCEY, M
    BISAGNI, E
    HUEL, C
    ZILBERFARB, D
    CROISY, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (01) : 65 - 71
  • [38] Synthesis of novel 2,3-dihydro-1,4-dioxino[2,3-g]quinoline derivatives as potential antitumor agents
    Vázquez, MT
    Romero, M
    Pujol, MD
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (05) : 949 - 956
  • [39] Design, Synthesis and Cytotoxicity Evaluation of New 2-Aryl-5, 6-Dihydropyrrolo[2, 1-a]Isoquinoline Derivatives as Topoisomerase Inhibitors
    Kakhki, Samaneh
    Shahosseini, Sorayya
    Zarghi, Afshin
    IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH, 2014, 13 : 71 - 77
  • [40] AZATRITERPENES .7. SYNTHESIS OF 2-ENO-[2,3-G]TETRAZOLO[1,5-A]PYRIMIDINES OF PENTACYCLIC TRITERPENES
    SUDHAKAR, B
    RAJARAM, P
    RAMAIAH, TS
    RAO, KL
    RAMRAJ, SK
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1987, 64 (11) : 712 - 713
12345