Ligand-free Pd(II)-catalyzed cyclization of α-chloroimino-N-arylamides to synthesis of quinoxalin-2(1H)-ones

被引:1
作者
Li, Dianjun [1 ,2 ]
Yang, Jinhui [1 ,2 ]
Fan, Xu [2 ]
机构
[1] Ningxia Univ, Sch Chem & Chem Engn, State Key Lab High Efficiency Utilizat Coal & Gre, Yinchuan 750021, Ningxia, Peoples R China
[2] Ningxia Univ, Sch Chem & Chem Engn, Yinchuan 750021, Ningxia, Peoples R China
基金
中国国家自然科学基金;
关键词
Quinoxalin-2(1H)-ones; Pd(II)-catalyzed; 2-(N-arylcarbamoyl)-2-chloroiminoacetate; alpha-Aryl-alpha-chloroimino-N-arylamides; Cyclization; CRAFTS ALLYLIC ALKYLATION; RADICAL CYCLIZATION; DERIVATIVES; QUINOXALINONES; HETEROCYCLES; DESIGN; POTENT;
D O I
10.1016/j.tetlet.2020.152556
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A ligand-free Pd(II)-catalyzed synthesis of quinoxalin-2(1H)-ones has been developed. Pd(TFA)(2) can induce ethyl 2-(N-arylcarbamoyl)-2-chloroiminoacetates to undergo cyclization to afford quinoxalin-2(1H)-one products in high yields in the presence of Na2CO3. This catalytic system is also effective to convert alpha-aryl-alpha-chloroimino-N-arylamides to the corresponding quinoxalin-2(1H)-one products via tandem N-Cl cleavage and N-arylation in moderate yields. The reaction described herein constitutes simple and effective approach towards quinoxalin-2(1H)-one derivatives. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数:5
相关论文
共 50 条
  • [21] An Efficient Domino Synthesis of Quinoxalin-2(1H)-ones via an SNAr/Coupling/Demesylation Reaction Catalyzed by Copper(I) as Key Step
    Chen, Dingben
    Bao, Weiliang
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 955 - 960
  • [22] Recent advances in the direct functionalization of quinoxalin-2(1H)-ones
    Ke, Qiumin
    Yan, Guobing
    Yu, Jian
    Wu, Xiangmei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (24) : 5863 - 5881
  • [23] Metal-Free Trifluoroalkylation of Quinoxalin-2(1H)-ones with Unactivated Alkenes and Langlois' Reagent
    Meng, Na
    Wang, Leilei
    Liu, Qishun
    Li, Qinyu
    Lv, Yufen
    Yue, Huilan
    Wang, Xiaojuan
    Wei, Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) : 6888 - 6896
  • [24] Synthesis of Quinoxalin-2(1H)-ones and Hexahydroquinoxalin-2(1H)-ones via Oxidative Amidation-Heterocycloannulation
    Raghunadh, Akula
    Tadiparthi, Krishnaji
    Meruva, Suresh Babu
    Murthy, V. Narayana
    Rao, L. Vaikunta
    Kumar, U. K. Syam
    SYNOPEN, 2020, 04 (03): : 55 - 61
  • [25] Silver-catalyzed decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo-carboxylic acids
    Zeng, Xiaobao
    Liu, Chulong
    Wang, Xingyong
    Zhang, Jianlan
    Wang, Xinyan
    Hu, Yuefei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (42) : 8929 - 8935
  • [26] Palladium-Catalyzed Coupling of N-Aminoazoles with 3-Halo-Substituted Quinolin-2(1H)-ones, Coumarins, Quinoxalin-2(1H)-ones, and Chromenes
    Thi Thanh Huyen Luong
    Brachet, Etienne
    Brion, Jean-Daniel
    Messaoudi, Samir
    Alami, Mouad
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (08) : 1771 - 1780
  • [27] Copper-catalyzed C3-amination of quinoxalin-2(1H)-ones: Using Selectfluor as a mild oxidant
    Pei, Congcong
    Chen, Xiaoyu
    Li, Linlin
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    TETRAHEDRON LETTERS, 2021, 83
  • [28] Electrochemical Dehydrogenative Cross-Coupling of Quinoxalin-2(1H)-ones with Amines for the Synthesis of 3-Aminoquinoxalinones
    Li, Ke-Jing
    Xu, Kun
    Liu, Yong-Guo
    Zeng, Cheng-Chu
    Sun, Bao-Guo
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) : 1033 - 1041
  • [29] Stereoselective Cyclization Cascade of Dihydroquinoxalinones by Visible-Light Photocatalysis: Access to the Polycyclic Quinoxalin-2(1H)-ones
    Tammisetti, Raviramanujayya
    Hong, Bor-Cherng
    Chien, Su-Ying
    Lee, Gene-Hsiang
    ORGANIC LETTERS, 2022, : 5155 - 5160
  • [30] Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones
    Sun, Kai
    Xiao, Fang
    Yu, Bing
    He, Wei-Min
    CHINESE JOURNAL OF CATALYSIS, 2021, 42 (11) : 1921 - 1943