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

被引：27

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

页码：213 / 218

页数：6

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 [J].

Aghapoor, Kioumars ;

Darabi, Hossein Reza ;

Mohsenzadeh, Farshid ;

Balavar, Yadollah ;

Daneshyar, Hesam .

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 [J].

Ajaikumar, S. ;

Pandurangan, A. .

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 [J].

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 .

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 [J].

Arumugam, P ;

Karthikeyan, G ;

Atchudan, R ;

Muralidharan, D ;

Perumal, PT .

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 [J].

Azarifar, Davood ;

Khosravi, Kaveh ;

Soleimanei, Fatemeh .

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 [J].

Bhosale, RS ;

Sarda, SR ;

Ardhapure, SS ;

Jadhav, WN ;

Bhusare, SR ;

Pawar, RP .

TETRAHEDRON LETTERS, 2005, 46 (42) :7183-7186

[9] On the shape selective acylation of 2-methoxynaphthalene over polymorph C of Beta (ITQ-17) [J].

Botella, P ;

Corma, A ;

Navarro, MT ;

Rey, F ;

Sastre, G .

JOURNAL OF CATALYSIS, 2003, 217 (02) :406-416

[10] Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives [J].

Cai, Jing-Jing ;

Zou, Jian-Ping ;

Pan, Xiang-Qiang ;

Zhang, Wei .

TETRAHEDRON LETTERS, 2008, 49 (52) :7386-7390

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