Synthesis of indolyl pyrroloindolines via a cascade arylation/cyclization of indole acetamides with 3-substituted indoles

被引:0
|
作者
Zhang, Wei [1 ]
Han, Shuai [1 ]
Zhang, Si-Yi [1 ]
Jiang, Dong-Xiao [1 ]
Chen, Jinjin [1 ]
Wang, Zhen [1 ]
Zeng, Yao-Fu [1 ]
机构
[1] Univ South China, Sch Pharmaceut Sci, Hengyang Med Sch, Hengyang 421001, Hunan, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 18期
基金
中国国家自然科学基金;
关键词
CONSTRUCTION; ALKALOIDS; AMAUROMINE; CATIONS;
D O I
10.1039/d4qo01118j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel TEA-mediated cascade arylation/cyclization reaction between indole acetamides and 3-substituted indoles has been developed. This method allows the synthesis of various indolyl pyrroloindolines in good yields under metal- and photocatalyst-free conditions. A gram-scale experiment and further derivatization of the products demonstrated the potential value of our method.
引用
下载
收藏
页码:5167 / 5171
页数:5
相关论文
共 50 条
  • [21] Organocatalytic aldol reaction of indole-3-carbaldehydes with ketones: synthesis of chiral 3-substituted indoles
    Guo, Qi-Xiang
    Wen, Wei
    Fu, Li-Na
    Zhang, Shun-En
    Zhang, Lan-Xi
    Liu, Yu-Wan
    Xu, Biao
    Xiong, Yan
    TETRAHEDRON LETTERS, 2013, 54 (35) : 4653 - 4655
  • [22] INSERTION OF ISOPRENE UNITS INTO INDOLE AND 3-SUBSTITUTED INDOLES IN AQUEOUS SYSTEMS
    BOCCHI, V
    CASNATI, G
    MARCHELLI, R
    TETRAHEDRON, 1978, 34 (07) : 929 - 932
  • [23] Enantioselective synthesis of C3 substituted benzofuroindolines via catalytic asymmetric [3+2] cyclization of 3-substituted indoles with p-benzoquinones
    Lu, Zhen-yu
    Lan, Wei-qiao
    Liu, Fang-yi
    Wang, Jun-yi
    Zhang, Xiao-mei
    Liao, Li-hua
    TETRAHEDRON LETTERS, 2021, 76
  • [24] Synthesis of New 3-Substituted Indole Derivatives
    Hassaneen, Huwaida M. E.
    Pagni, Richard M.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2010, 65 (12): : 1491 - 1497
  • [25] The syntheses of 3-substituted 4-(pyridin-2-ylthio)indoles via Leimgruber-Batcho indole synthesis
    Srisook, E
    Chi, DY
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (06): : 895 - 899
  • [26] Construction of Indole Structure on Pyrroloindolines via AgNTf2-Mediated Amination/Cyclization Cascade: Application to Total Synthesis of (+)-Pestalazine B
    Hakamata, Hiroyuki
    Ueda, Hirofumi
    Tokuyama, Hidetoshi
    ORGANIC LETTERS, 2019, 21 (11) : 4205 - 4209
  • [27] Novel synthesis of 3-substituted indoles and carbazoles.
    Söderberg, BC
    Turner, MR
    Scott, TL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U102 - U102
  • [28] SYNTHESIS OF 3-SUBSTITUTED INDOLES STARTING FROM ISATIN
    BERGMAN, J
    ACTA CHEMICA SCANDINAVICA, 1971, 25 (04): : 1277 - &
  • [29] UV study of the protonation of indole and 3-substituted indoles in perchloric acid media
    Andonovski, B
    Spirevska, I
    Nikolovski, A
    CROATICA CHEMICA ACTA, 1996, 69 (03) : 1201 - 1213
  • [30] THE FORMATION OF 1-SUBSTITUTED AND 3-SUBSTITUTED INDOLES IN THE REACTION BETWEEN INDOLE AND SODIUM GLYOXYLATE
    AMATGUERRI, F
    MARTINEZUTRILLA, R
    PASCUAL, C
    CHEMISTRY LETTERS, 1981, (04) : 511 - 514