I2-Promoted sp3 C-H Oxidation/Annulation Sequences for the Synthesis of Indoloquinolines from 2-(1H-indol-2-yl)anilines and Aryl Methyl Ketones

被引：4
|
作者：
Arockiaraj, Mariyaraj [1 ]
Rajeshkumar, Venkatachalam [1 ]
机构：
[1] Natl Inst Technol Warangal, Dept Chem, Organ Synth & Catalysis Lab, Hanumakonda 506004, Telangana, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 11期
关键词：
Indoloquinolines; Iodine; sp(3) C-H Oxidation; Annulation; Aryl methyl ketones; GAMMA-CARBOLINE ANALOGS; ISOCRYPTOLEPINE ANALOGS; CASCADE; INHIBITORS; OXIDATION; POTENT;
D O I：
10.1002/adsc.202400023
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An iodine/DMSO-promoted approach has been developed for the synthesis of indoloquinolines via a sequential sp(3) C-H oxidation/intramolecular cyclization using 2-(1H-indol-2-yl)anilines and aryl methyl ketones. A wide range of aryl methyl ketones, including drugs and complex bioactive molecule-derived substrates were compatible in the present reaction with yields in the range of 30-96%. This protocol proceeds through sp(3) C-H oxidation of aryl methyl ketones to phenylglyoxals, subsequent imine formation, and cyclization to furnish the indoloquinolines. Further, the reaction is applicable for gram-scale synthesis and is operationally simple.
引用
收藏
页码：2557 / 2564
页数：8
相关论文
共 50 条
  • [31] Ethyl 2-{2-[(1-methyl-2-phenyl-1H-indol-3-yl)diazenyl]thiazol-4-yl}acetate
    Seferoglu, Zeynel
    Hokelek, Tuncer
    Sahin, Ertan
    Saylam, Aytul
    Ertan, Nermin
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O5488 - O5489
  • [32] Synthesis, crystal structure and DFT study of methyl 2-(1H-indol-3-yl)-2-oxoacetate
    Yang, Yan
    Li, Jin-Lan
    Ma, Li-Xue
    Yang, Bai-Hui
    Zhou, Zhi-Xu
    Ji, Chun
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2023, 766 (01) : 90 - 99
  • [33] Microwave assisted sp3 C-H activation of 2-methyl-quinoline and addition to electron deficient ketones
    Rao, Nalajala Nageswara
    Mali, Prakash Rambhau
    Meshram, H. M.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2014, 53 (09): : 1153 - 1158
  • [34] Crystal structure of N-{[3-bromo-1-(phenylsulfonyl)-1H-indol-2-yl]methyl}-benzenesulfonamide
    Umadevi, M.
    Raju, P.
    Yamuna, R.
    Mohanakrishnan, A. K.
    Chakkaravarthi, G.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O756 - U403
  • [35] Ethyl 3-{2-[(3-Methyl-1H-indol-2-yl)carbonyl]hydrazinylidene}-butanoate
    Farghaly, Thoraya A.
    Gomha, Sobhi M.
    MOLBANK, 2012, (01)
  • [36] I2-DMSO catalyzed synthesis of 1,2,2-triarylethanones via dual C-H activation of aryl methyl ketones
    Reddy, M. Raghavender
    Rao, N. Nageswara
    Ramakrishna, K.
    Meshram, H. M.
    TETRAHEDRON LETTERS, 2014, 55 (11) : 1898 - 1901
  • [37] Rhodium(iii)-catalyzed regioselective oxidative annulation of anilines and allylbenzenes via C(sp3)-H/C(sp2)-H bond cleavage
    Liu, Yunqi
    Yang, Yudong
    Wang, Chunxia
    Wang, Zhishuo
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2019, 55 (08) : 1068 - 1071
  • [38] I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C-H functionalization
    Vadagaonkar, Kamlesh S.
    Kalmode, Hanuman P.
    Murugan, Kaliyappan
    Chaskar, Atul C.
    RSC ADVANCES, 2015, 5 (08): : 5580 - 5590
  • [39] 2-(TRIBUTYLSTANNYL)-1-([2-(TRIMETHYLSILYL)ETHOXY]METHYL)-1H-INDOLE - SYNTHESIS AND USE AS A 1H-INDOL-2-YL-ANION EQUIVALENT
    PALMISANO, G
    SANTAGOSTINO, M
    HELVETICA CHIMICA ACTA, 1993, 76 (06) : 2356 - 2366
  • [40] Synthesis of 6H-isoindolo[2,1-a]indol-6-ones via Pd-catalyzed cycloaminocarbonylation of 2-(1H-indol-2-yl)phenyl tosylates with CO
    Liu, Bin
    Lai, Chunbo
    Zhang, Chunlei
    Zhou, Xigeng
    TETRAHEDRON, 2018, 74 (07) : 752 - 757
12345