Catalytic application of recyclable silica-supported bismuth(III) chloride in the benzo[N,N]-heterocyclic condensation

被引:23
作者
Aghapoor, Kioumars [1 ]
Mohsenzadeh, Farshid [1 ]
Shakeri, Atena [1 ]
Darabi, Hossein Reza [1 ]
Ghassemzadeh, Mitra [1 ]
Neumueller, Bernhard [2 ]
机构
[1] Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
[2] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
关键词
BiCl3/SiO2; Heterogeneous Lewis acid catalyst; Benzo[N; N]-heterocyclic condensation; SOLID ACID CATALYST; ORGANIC-SYNTHESIS; QUINOXALINE DERIVATIVES; ROOM-TEMPERATURE; HETEROGENEOUS CATALYSIS; EFFICIENT; NANOPARTICLES; CHEMISTRY; WATER; 1,4-DI-N-OXIDE;
D O I
10.1016/j.jorganchem.2013.06.037
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Silica-supported bismuth(III) chloride (BiCl3/SiO2) has been successfully employed in the condensation of 1,2-dicarbonyls with a variety of arene-1,2-diamines bearing either electron withdrawing or donating functional groups. The catalyzed reaction proceeded smoothly under ambient temperature in methanol to give the corresponding quinoxaline and pyrido[2,3-b]pyrazine compounds in good to excellent yields. The catalyst exhibited remarkable reusable activity and higher catalytic performance than homogeneous BiCl3. A plausible mechanism for the catalytic action of BiCl3/SiO2 has been introduced. Moreover, the crystal structure of the prepared unsymmetrical benzo[N,N]-heterocycles has been determined by single crystal X-ray diffraction. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:170 / 178
页数:9
相关论文
共 54 条
  • [21] Gaspard-Iloughmane H., 2006, TRENDS ORGANIC CHEM, V11, P65
  • [22] Recent advances in bismuth-catalyzed organic synthesis
    Hua, Ruimao
    [J]. CURRENT ORGANIC SYNTHESIS, 2008, 5 (01) : 1 - 27
  • [23] Montmorillonite K-10: An efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water
    Huang, Tai-kun
    Wang, Rui
    Shi, Lin
    Lu, Xiao-xia
    [J]. CATALYSIS COMMUNICATIONS, 2008, 9 (06) : 1143 - 1147
  • [24] Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions
    Jafarpour, Maasoumeh
    Rezaeifard, Abdolreza
    Danehchin, Maryam
    [J]. APPLIED CATALYSIS A-GENERAL, 2011, 394 (1-2) : 48 - 51
  • [25] Solvent free synthesis of quinoxalines, dipyridophenazines and chalcones under microwave irradiation with sulfated Degussa titania as a novel solid acid catalyst
    Krishnakumar, B.
    Swaminathan, M.
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 350 (1-2) : 16 - 25
  • [26] An efficient protocol for the green synthesis of quinoxaline and dipyridophenazine derivatives at room temperature using sulfated titania
    Krishnakumar, B.
    Velmurugan, R.
    Jothivel, S.
    Swaminathan, M.
    [J]. CATALYSIS COMMUNICATIONS, 2010, 11 (12) : 997 - 1002
  • [27] Applications of heterogeneous catalytic processes to the environmentally friendly synthesis of fine chemicals
    Kwak, BS
    [J]. CATALYSIS SURVEYS FROM ASIA, 2005, 9 (02) : 103 - 116
  • [28] An efficient green synthesis of quinoxaline derivatives using carbon-doped MoO3-TiO2 as a heterogeneous catalyst
    Lande, Machhindra
    Navgire, Madhukar
    Rathod, Sandip
    Katkar, Santosh
    Yelwande, Ajeet
    Arbad, Balasaheb
    [J]. JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2012, 18 (01) : 277 - 282
  • [29] Le Roux C, 2002, SYNLETT, P181
  • [30] Applications of bismuth(III) compounds in organic synthesis
    Leonard, NM
    Wieland, LC
    Mohan, RS
    [J]. TETRAHEDRON, 2002, 58 (42) : 8373 - 8397