Heterogeneous SnCl2/SiO2 versus Homogeneous SnCl2 Acid Catalysis in the Benzo[N,N]-heterocyclic Condensation

被引:26
作者
Darabi, Hossein Reza [1 ,2 ]
Aghapoor, Kioumars [1 ]
Mohsenzadeh, Farshid [1 ]
Jalali, Mohammad Reza [1 ]
Talebian, Shiva [1 ]
Ebadi-Nia, Leila [1 ]
Khatamifar, Ehsan [2 ]
Aghaee, Ali [2 ]
机构
[1] Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
[2] Shifa Pharmed Ind Grp Co, Karaj, Iran
来源
BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2011年 / 32卷 / 01期
关键词
SnCl2/SiO2; Heterogeneous Lewis acid catalyst; Sustainability; Benzo[N; N]-heterocyclic condensation; SOLID ACIDS; QUINOXALINE DERIVATIVES; EFFICIENT SYNTHESIS; MOLECULAR-IODINE; CONVENIENT; CHEMISTRY; CHLORIDE; PROTOCOL; SYSTEM; WATER;
D O I
10.5012/bkcs.2011.32.1.213
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The scope of homogeneous Lewis acid-catalyzed benzo[N,N]-heterocyclic condensation was expanded to include the use of various metal salts not reported in the literature and SnCl2 center dot 2H(2)O was finally selected. Among various solid supports activated with SnCl2, heterogeneous SnCl2/SiO2 proved to be the most effective and significantly higher conversions were achieved compared to SnCl2 center dot 2H(2)O itself. The results of TG-DTA and BET indicated that dispersed SnCl2 coordinates with surface hydroxyl groups of silica leading to formation of stable Lewis acid sites. Low catalyst loading, operational simplicity, practicability and applicability to various substrates render this eco-friendly approach as an interesting alternative to previously applied procedures.
引用
收藏
页码:213 / 218
页数:6
相关论文
共 51 条
  • [1] Aghapoor K, 2005, Z NATURFORSCH B, V60, P901
  • [2] Zirconium(IV) chloride as versatile catalyst for the expeditious synthesis of quinoxalines and pyrido[2,3-b]pyrazines under ambient conditions
    Aghapoor, Kioumars
    Darabi, Hossein Reza
    Mohsenzadeh, Farshid
    Balavar, Yadollah
    Daneshyar, Hesam
    [J]. TRANSITION METAL CHEMISTRY, 2010, 35 (01) : 49 - 53
  • [3] Efficient synthesis of quinoxaline derivatives over ZrO2/MxOy (M = Al, Ga, In and La) mixed metal oxides supported on MCM-41 mesoporous molecular sieves
    Ajaikumar, S.
    Pandurangan, A.
    [J]. APPLIED CATALYSIS A-GENERAL, 2009, 357 (02) : 184 - 192
  • [4] Alam MM, 2006, LETT ORG CHEM, V3, P187
  • [5] Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation
    Alfonsi, Kim
    Colberg, Juan
    Dunn, Peter J.
    Fevig, Thomas
    Jennings, Sandra
    Johnson, Timothy A.
    Kleine, H. Peter
    Knight, Craig
    Nagy, Mark A.
    Perry, David A.
    Stefaniak, Mark
    [J]. GREEN CHEMISTRY, 2008, 10 (01) : 31 - 36
  • [6] A simple, efficient and solvent-free protocol for the Friedlander synthesis of quinolines by using SnCl2 • 2H2O
    Arumugam, P
    Karthikeyan, G
    Atchudan, R
    Muralidharan, D
    Perumal, PT
    [J]. CHEMISTRY LETTERS, 2005, 34 (03) : 314 - 315
  • [7] Stannous Chloride Dihydrate: A Novel and Efficient Catalyst for the Synthesis of gem-Dihydroperoxides from Ketones and Aldehydes
    Azarifar, Davood
    Khosravi, Kaveh
    Soleimanei, Fatemeh
    [J]. SYNTHESIS-STUTTGART, 2009, (15): : 2553 - 2556
  • [8] An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst
    Bhosale, RS
    Sarda, SR
    Ardhapure, SS
    Jadhav, WN
    Bhusare, SR
    Pawar, RP
    [J]. TETRAHEDRON LETTERS, 2005, 46 (42) : 7183 - 7186
  • [9] On the shape selective acylation of 2-methoxynaphthalene over polymorph C of Beta (ITQ-17)
    Botella, P
    Corma, A
    Navarro, MT
    Rey, F
    Sastre, G
    [J]. JOURNAL OF CATALYSIS, 2003, 217 (02) : 406 - 416
  • [10] Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives
    Cai, Jing-Jing
    Zou, Jian-Ping
    Pan, Xiang-Qiang
    Zhang, Wei
    [J]. TETRAHEDRON LETTERS, 2008, 49 (52) : 7386 - 7390