Iridium-Catalyzed Cascade Reaction of Sulfoxonium Ylides with o-Aminoaryl Aldehydes for the Synthesis of 2-Acylindoles

被引:0
作者
Tong, Yixin [1 ]
Mi, E. [1 ]
Zhou, Li [1 ]
Wang, Xiabin [1 ]
Xiong, Biao [1 ]
机构
[1] Nantong Univ, Sch Pharm, 19 Qixiu Rd, Nantong 226001, Jiangsu, Peoples R China
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 40期
基金
中国国家自然科学基金;
关键词
2-Acylindoles; Sulfoxonium ylides; Iridium-; catalyzed; N-H Insertion; Annulation; 2-SUBSTITUTED INDOLES; BIOLOGICAL EVALUATION; SULFUR YLIDES; DERIVATIVES; ANNULATION; CYCLOADDITION; ACTIVATION; PYRROLES; POTENT;
D O I
10.1002/slct.202303078
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Acylindoles possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, a method to achieve 2-acylindoles from sulfoxonium ylides with o-aminoaryl aldehydes catalysed by Iridium has been developed with the merits of broad substrate scope, good functional tolerance, high efficiency and operational simplicity, which provides an alternative way to access functionalized indoles.
引用
收藏
页数:5
相关论文
共 69 条
  • [1] NOVEL SYNTHESIS OF INDOLES VIA PALLADIUM-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF ORTHO-NITROSTYRENE DERIVATIVES
    AKAZOME, M
    KONDO, T
    WATANABE, Y
    [J]. CHEMISTRY LETTERS, 1992, (05) : 769 - 772
  • [2] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds
    Barday, Manuel
    Janot, Christopher
    Halcovitch, Nathan R.
    Muir, James
    Aissa, Christophe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 13117 - 13121
  • [3] Baykal A., 2019, Eur. J. Org. Chem, V5, P1145
  • [4] Indole, a core nucleus for potent inhibitors of tubulin polymerization
    Brancale, Andrea
    Silvestri, Romano
    [J]. MEDICINAL RESEARCH REVIEWS, 2007, 27 (02) : 209 - 238
  • [5] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones
    Cai, Libo
    Zhu, Xiaoyi
    Chen, Jiayi
    Lin, Aijun
    Yao, Hequan
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21): : 3688 - 3692
  • [6] Substrate-Controlled Transformation of Azobenzenes to Indazoles and Indoles via Rh(III)-Catalysis
    Cai, Shangjun
    Lin, Songyun
    Yi, Xiangli
    Xi, Chanjuan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01) : 512 - 520
  • [7] α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
    Caiuby, Clarice A. D.
    de Jesus, Matheus P.
    Burtoloso, Antonio C. B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) : 7433 - 7445
  • [8] Design, syntheses, biological evaluation, and docking studies of 2-substituted 5-methylsulfonyl-1-phenyl-1H-indoles:: Potent and selective in vitro cyclooxygenase-2 inhibitors
    Cruz-Lopez, Olga
    Diaz-Mochon, Juan Jose
    Campos, Joaquin M.
    Entrena, Antonio
    Nunez, Maria T.
    Labeaga, Luis
    Orjales, Aurelio
    Gallo, Miguel A.
    Espinosa, Antonio
    [J]. CHEMMEDCHEM, 2007, 2 (01) : 88 - 100
  • [9] Ruthenium- catalyzed synthesis of indole derivatives from N- aryl-2-aminopyridines and alpha- carbonyl sulfoxonium ylides
    Cui, Xin-Feng
    Ban, Zi-Hui
    Tian, Wa-Fa
    Hu, Fang-Peng
    Zhou, Xiao-Qiang
    Ma, Hao-Jie
    Zhan, Zhen-Zhen
    Huang, Guo-Sheng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (02) : 240 - 243
  • [10] Indole-2-Carboxaldehyde: An Emerging Precursor for the Construction of Diversified Imperative Skeleton
    Das, Arunima
    Thakur, Seema
    Das, Tapas
    [J]. CHEMISTRYSELECT, 2021, 6 (18): : 4591 - 4619