Mild Bronsted basic ionic liquids catalyzed three component synthesis of pyrazolo[1,2-a][1,2,4]triazole-1,3-dione and 2-amino-3-cyano-5,10-dioxo-4-phenyl-5,10-dihydro-4H-benzo[g]chromene derivatives

被引:13
|
作者
Shaterian, H. R. [1 ]
Kangani, M. [1 ]
机构
[1] Univ Sistan & Baluchestan, Fac Sci, Dept Chem, Zahedan, Iran
关键词
2-hydroxyethylammonium formate; 2-hydroxyethylammonium acetate; Ionic liquids; Catalyst; HETEROGENEOUS CATALYST; EFFICIENT;
D O I
10.1016/j.scient.2012.11.019
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Pyrazolo[1,2-a][1,2,4]triazole-1,3-dione derivatives were synthesized via a three component reaction of arylaldehydes, 4-phenylurazole and malononitrile in the presence of a catalytic amount of 2-hydroxyethylammonium formate and 2-hydroxyethylammonium acetate as effective mild basic ionic liquids, without using any additional co-catalyst, under solvent-free conditions at room temperature in good yields. Ionic liquids as catalysts were recovered and reused. In addition, the preparation of 2-amino-3-cyano-5,10-dioxo-4-phenyl-5,10-dihydro-4H-benzo[g]chromene derivatives from the reaction of arylaldehydes, malononitrile and 2-hydroxy-1,4-dihydronaphthalene-1,4-dione under solvent-free conditions at ambient temperature in the presence of mentioned catalysts is reported. (C) 2013 Sharif University of Technology. Production and hosting by Elsevier B.V. All rights reserved.
引用
收藏
页码:571 / 579
页数:9
相关论文
共 50 条
  • [1] Preparation of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene and hydroxyl naphthalene-1,4-dione derivatives
    Fahime Khorami
    Hamid Reza Shaterian
    Research on Chemical Intermediates, 2015, 41 : 3171 - 3191
  • [2] Preparation of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene and hydroxyl naphthalene-1,4-dione derivatives
    Khorami, Fahime
    Shaterian, Hamid Reza
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (05) : 3171 - 3191
  • [3] 2-Amino-4-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile
    Zhang, Jinpeng
    Zhang, Xiaohong
    Yan, Shu
    Ma, Ning
    Tu, Shujiang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O5 - U1298
  • [4] One-Pot Synthesis of 2-Amino-5,10-dihydro-5,10-dioxo-4-phenyl-4H-benzo[g]chromene Derivatives Catalyzed by ZnCl2
    Srinivas, V.
    Rao, V. Rajeswar
    SYNTHETIC COMMUNICATIONS, 2011, 41 (06) : 806 - 811
  • [5] Ethyl 2-amino-4-(3-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxylate
    Hu, Xiao
    Lei, Song
    Yao, Chang-Sheng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1324 - U2256
  • [6] Facile and convenient synthesis of 2-amino-5,10-dioxo-4-aryl-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile derivatives by electrocatalytically chemical transformation
    Vafajoo, Zahra
    Kordestani, Davood
    Vafajoo, Saba
    IRANIAN CHEMICAL COMMUNICATION, 2018, 6 (03) : 293 - 299
  • [7] Zeolite-catalyzed synthesis of pyrazolo[1,2-a][1,2,4]triazole-1,3-dione derivatives as anti-breast cancer agents
    Nejat, Razieh
    Mahjoub, Mohammad Amin
    Hekmatian, Zahra
    Javidi, Mohammad Amin
    Babashah, Sadegh
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (05) : 1133 - 1143
  • [8] Zeolite-catalyzed synthesis of pyrazolo[1,2-a][1,2,4]triazole-1,3-dione derivatives as anti-breast cancer agents
    Razieh Nejat
    Mohammad Amin Mahjoub
    Zahra Hekmatian
    Mohammad Amin Javidi
    Sadegh Babashah
    Journal of the Iranian Chemical Society, 2018, 15 : 1133 - 1143
  • [9] A Green Route for the Synthesis of 2-Amino-5,10-dioxo-4-aryl-5,10-dihydro-4H-benzo[g]chromene-3-carbonitriles Using L-Proline as a Basic Organocatalyst
    Daloee, Toktam Shiebani
    Behbahani, Farahnaz K.
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (03) : 681 - 689
  • [10] Effective preparation of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo [g]chromene and hydroxyl naphthalene-1,4-dione derivatives under ambient and solvent-free conditions
    Shaterian, Hamid Reza
    Mohammadnia, Majid
    JOURNAL OF MOLECULAR LIQUIDS, 2013, 177 : 353 - 360