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 40 条
  • [1] New Route to the Synthesis of the Isocryptolepine Alkaloid and Its Related Skeletons Using a Modified Pictet-Spengler Reaction
    Agarwal, Piyush K.
    Sawant, Devesh
    Sharma, Sunil
    Kundu, Bijoy
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (02) : 292 - 303
  • [2] Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines
    Aksenov, Alexander V.
    Aksenov, Dmitrii A.
    Griaznov, Georgii D.
    Aksenov, Nicolai A.
    Voskressensky, Leonid G.
    Rubin, Michael
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) : 4325 - 4332
  • [3] In Vitro and In Vivo Antitumor Activity of Indolo[2,3-b] Quinolines, Natural Product Analogs from Neocryptolepine Alkaloid
    Altwaijry, Najla
    El-Ghlban, Samah
    El Sayed, Ibrahim E. -T.
    El-Bahnsawye, Mohamed
    Bayomi, Asmaa I.
    Samaka, Rehab M.
    Shaban, Elkhabiry
    Elmongy, Elshaymaa I.
    El-Masry, Thanaa A.
    Ahmed, Hytham M. A.
    Attallah, Nashwah G. M.
    [J]. MOLECULES, 2021, 26 (03):
  • [4] I2-Catalyzed Oxidative Cross-Coupling Reaction of Methyl Ketones and 2-(2-Aminophenyl) Benzimidazole: Facile Access to Benzimidazo[1,2-c]quinazoline
    Ambethkar, Sethurajan
    Kalaiselvi, Mariappan
    Ramamoorthy, Jaganathan
    Padmini, Vediappen
    [J]. ACS OMEGA, 2018, 3 (05): : 5021 - 5028
  • [5] Visible-Light-Induced Aerobic Intramolecular Cyclization of (2-Aminophenyl)(1H-indol-1-yl)methanones: Direct Access to Bioactive Tryptanthrin and its Derivatives
    Arockiaraj, Mariyaraj
    Singh, Gargi
    Marupalli, Sasi Sree
    Rajeshkumar, Venkatachalam
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (10) : 1654 - 1659
  • [6] Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents
    Aroonkit, Pasuk
    Thongsornkleeb, Charnsak
    Tummatorn, Jumreang
    Krajangsri, Suppachai
    Mungthin, Mathirut
    Ruchirawat, Somsak
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 94 : 56 - 62
  • [7] Palladium-Catalyzed C-2 and C-3 Dual C-H Functionalization of Indoles: Synthesis of Fluorinated Isocryptolepine Analogues
    Chen, Chen
    Wang, Yuebo
    Shi, Xiaonan
    Sun, Wan
    Zhao, Jinghui
    Zhu, Yan-Ping
    Liu, Liying
    Zhu, Bolin
    [J]. ORGANIC LETTERS, 2020, 22 (11) : 4097 - 4102
  • [8] Condition-Dependent Selective Synthesis of Indolo[1,2-c]quinazolines and Indolo[3,2-c]quinolines from and Sulfoxonium Ylides
    Chen, Guang
    Cai, Xinyuan
    Zhang, Xinying
    Fan, Xuesen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15) : 9815 - 9828
  • [9] Design, Synthesis, and Antimicrobial Activity of Quindoline Derivatives Inspired by the Cryptolepine Alkaloid
    Chu, Qing-Ru
    He, Ying-Hui
    Tang, Chen
    Zhang, Zhi-Jun
    Luo, Xiong-Fei
    Zhang, Bao-Qi
    Zhou, Yong
    Wu, Tian-Lin
    Du, Sha-Sha
    Yang, Cheng-Jie
    Liu, Ying-Qian
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2022, 70 (09) : 2851 - 2863
  • [10] β-Carboline alkaloid monomers and dimers: Occurrence, structural diversity, and biological activities
    Dai, Jiangkun
    Dan, Wenjia
    Schneider, Uwe
    Wang, Junru
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 157 : 622 - 656
1234