Eosin Y-catalyzed one-pot synthesis of spiro[4H-pyran-oxindole] under visible light irradiation

被引：57
作者：
Chen, Meng-Nan [1 ]
Di, Jia-Qi [1 ]
Li, Jiao-Mian [1 ]
Mo, Li-Ping [1 ]
Zhang, Zhan-Hui [1 ]
机构：
[1] Hebei Normal Univ, Coll Chem & Mat Sci, Natl Demonstrat Ctr Expt Chem Educ, Hebei Key Lab Organ Funct Mol, Shijiazhuang 050024, Hebei, Peoples R China
来源：
TETRAHEDRON | 2020年 / 76卷 / 14期
基金：
中国国家自然科学基金;
关键词：
Spiro [4H-pyran-oxindole; Linear 1,3-dicarbonyl compounds; Multicomponent reaction; Eosin Y; Visible light; MEDIATED RADICAL ARYLDIFLUOROACETYLATION; MULTICOMPONENT REACTIONS; 3-COMPONENT SYNTHESIS; FUNCTIONALIZED SPIROOXINDOLE; EFFICIENT SYNTHESIS; N-ARYLACRYLAMIDES; HIGHLY EFFICIENT; L-PROLINE; DERIVATIVES; METAL;
D O I：
10.1016/j.tet.2020.131059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and simple synthetic approach has been developed for the preparation of biologically interesting spiro[oxindole-3,4'-(4'H-pyran)] derivatives via visible light-mediated one-pot, three-component reaction of isatins, 1,3-dicarbonyl compounds and malononitrile by using an inexpensive organic dye, Na-2 eosin Y, as the photocatalyst in aqueous ethyl lactate at ambient temperature. The substrate scope of this three-component reaction is expanded to linear 1,3-dicarbonyl compounds as viable starting materials. All rights reserved. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：11
相关论文
共 50 条
  • [31] Visible-light Driven Eosin Y Catalyzed C(sp2)-H Functionalization/C-O Bond Formation for Synthesis of Benzoxazoles
    Mishra, Mangla
    Srivastava, Vishal
    Singh, Pravin K.
    Singh, Praveen P.
    CROATICA CHEMICA ACTA, 2023, 95 (01) : 25 - 30
  • [32] Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B12 Model Complex under Aerobic Conditions
    Tian, Hui
    Shimakoshi, Hisashi
    Ono, Toshikazu
    Hisaeda, Yoshio
    CHEMPLUSCHEM, 2019, 84 (03): : 237 - 240
  • [33] [BMIM]Cl Catalyzed One-Pot Synthesis of α-Aminophosphonate Derivatives Containing a 4-Phenoxyquinazoline Moiety under Microwave Irradiation
    Bai Song
    Song Baoan
    Bhadury, Pinaki S.
    Yang Song
    Hu Deyu
    Xue Wei
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (01) : 109 - 117
  • [34] Visible-Light-Driven One-Pot Synthesis of Benzimidazoles, Benzothiazoles, and Quinazolinones Catalyzed by Scalable and Reusable Ba-Doped CoMoO4 Nanoparticles Under Air Atmosphere
    Abinaya, Ramanjulu
    Elavarasan, Selvaraj
    Binish, B.
    Rahulan, K. Mani
    Balasubramanian, Kalpattu K.
    Manokaran, Kamaraj
    Varathan, Elumalai
    Baskar, Baburaj
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (04)
  • [35] A convenient one-pot synthesis of thiopyrano[4,3-b]pyran derivatives under LiOH•H2O/EtOH/ultrasonic conditions
    Pourabdi, Ladan
    Osati, Fatemeh
    Mojtahedi, Mohammad M.
    Abaee, Saeed M.
    JOURNAL OF SULFUR CHEMISTRY, 2017, 38 (01) : 34 - 42
  • [36] One-pot multicomponent photo-induced eosin-Y catalyzed synthesis of 2-amino oxa/thiazine derivatives
    Garima, Km
    Srivastava, Vishal
    Singh, Praveen P.
    Singh, Pravin K.
    TETRAHEDRON LETTERS, 2024, 152
  • [37] Three-Component Synthesis of Spiro[Indoline-3,4′-Pyrano[3,2-b]Pyran]-2,8′-Diones Using a One-Pot Reaction
    Rahmati, Abbas
    Khalesi, Zahra
    Kenarkoohi, Tahmineh
    COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2014, 17 (02) : 132 - 140
  • [38] Enantioselective synthesis of spiro[4H-pyran-3,3′-oxindole] derivatives catalyzed by cinchona alkaloid thioureas: Significant water effects on the enantioselectivity
    Konda, Swapna
    Jakkampudi, Satish
    Arman, Hadi D.
    Zhao, John C-G
    SYNTHETIC COMMUNICATIONS, 2019, 49 (21) : 2971 - 2982
  • [39] Supported molybdenum on graphene oxide/Fe3O4: An efficient, magnetically separable catalyst for one-pot construction of spiro-oxindole dihydropyridines in deep eutectic solvent under microwave irradiation
    Zhang, Mo
    Liu, Yu-Heng
    Shang, Ze-Ren
    Hu, Hai-Chuan
    Zhang, Zhan-Hui
    CATALYSIS COMMUNICATIONS, 2017, 88 : 39 - 44
  • [40] One-pot loading of cadmium sulfide onto tungsten carbide for efficient photocatalytic H2 evolution under visible light irradiation
    Lei, Yonggang
    Ng, Kim Hoong
    Zhang, Yingzhen
    Li, Zengxing
    Xu, Shen
    Huang, Jianying
    Lai, Yuekun
    CHEMICAL ENGINEERING JOURNAL, 2022, 434
12345