Characterization of Catalyst: Comparison of BrØnsted and Lewis Acidic Power in Boron Sulfonic Acid as a Heterogeneous Catalyst in Green Synthesis of Quinoxaline Derivatives

Sajjadifar, Sami; Pal, Kaushik; Jabbari, Hadi; Pouralimardan, Omidali; Divsar, Faten; Mohammadi-Aghdam, Sarvin; Amini, Issa; Hamidi, Hoda

doi:10.22034/chemm.2018.147943.1086

|
|
|
How to cite
RIS EndNote BibTeX APA MLA Harvard Vancouver
|
Share

	Characterization of Catalyst: Comparison of BrØnsted and Lewis Acidic Power in Boron Sulfonic Acid as a Heterogeneous Catalyst in Green Synthesis of Quinoxaline Derivatives
Article 6, Volume 3, Issue 2. pp. 145-275, March and April 2019, Page 226-236 PDF (1.02 MB)
Document Type: Original Article
DOI: 10.22034/chemm.2018.147943.1086
Authors
Sami Sajjadifar ¹; Kaushik Pal ²; Hadi Jabbari¹; Omidali Pouralimardan ¹; Faten Divsar ¹; Sarvin Mohammadi-Aghdam¹; Issa Amini¹; Hoda Hamidi ¹
¹Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
²Department of Nanotechnology, Bharath University, BIHER Research Park, Chennai, Tamil Nadu 600073, India
Receive Date: 08 September 2018, Revise Date: 27 October 2018, Accept Date: 28 October 2018
Abstract
A simple, highly efficient and green procedure for the condensation of aryl and alkyl 1,2-diamines with α-diketones in the presence of catalytic amount of boron sulfonic acid (BSA) and silica trimethyl borat (STMB) and silica triisopropyl borate (STIPB), as two novel heterogeneous Lewis acid catalysts at room temperature, is described. In this method, we proved that the BrØnsted acidic power of boron sulfonic acid (BSA) is more important than its Lewis acidity. Using this method, quinoxaline derivatives as biologically interesting compounds are produced in high to excellent yields.
Graphical Abstract

Keywords
Quinoxaline; Boron sulfonic acid; Trimethyl borate; Triisopropyl borate; SBSA; STMB; STIPB
Main Subjects
Organic Chemistry


References
[1] Brock E.D., Lewis D.M., Yousaf T.I., Harper H.H., WO 9951688, 1999 [2] Gazit A., App H., McMahon G., Chen J., Levitzki A., Bohmer F.D. J. Med. Chem., 1996, 39:2170 [3] Sehlstedt U., Aich P., Bergman J., Vallberg H., Norden B., Graslund A. J. Mol. Biol., 1998, 278:31 [4] Dailey S., Feast J.W., Peace R.J., Sage I.C., Till S., Wood E.L. J. Mater. Chem., 2011, 11:2238 [5] O’Brien D., Weaver M.S., Lidzey D.G., Bradley D.D.C. Appl. Phys. Lett., 1996, 69:881 [6] Yamamoto T., Sugiyama K., Kushida T., Inoue T., Kanbara T. J. Am. Chem. Soc., 1996, 118:3930 [7] Yamamoto T., Zhou Z.H., Kanbara T., Shimura M., Kizu K., Maruyama T., Nakamura Y., Fukuda T., Lee B.L., Ooba N., Tomaru S., Kurihara T., Kanno T., Kubota K., Sasaki S. J. Am. Chem. Soc., 1996, 118:10389 [8] Nurulla I., Yamaguchi I., Yamamoto T. Polym. Bull., 2000, 44:231 [9] Yamamoto T., Lee B.L., Kokubo H., Kishida H., Hirota K., Wakabayashi T., Okamoto H. Macromol. Rapid Commun., 2003, 24:440 [10] Dell A., William D.H., Morris H.R., Smith G.A., Feeney J., Roberts G.C.K. J. Am. Chem. Soc., 1975, 97:2497 [11] Bailly C., Echepare S., Gago F., Waring M.J. Anti. Cancer Drug Des., 1999, 15:291 [12] Eicher T., Hauptmann S. The Chemistry of Heterocycles; Thieme: New York, 1995; 417, 434 [13] Barluenga J., Aznar F., Liz R., Cabal M.P. Synthesis, 1985, 1985:313 [14] Petukhov P.A., Tkachev A.V. Tetrahedron, 1997, 53:9761 [15] Brown D.J. Quinoxalines: Supplement II., Eds.; John Wiley& Sons: New Jersey, 2004 [16] Heravi M.M., Taheri S., Bakhtiari K., Oskooie H.A. Catal Commun., 2007, 8:1341 [17] More S.V., Sastry M.N.V., Yao C.F. Green Chem., 2006, 8:91 [18] Mao L., Sakurai H., Hirao T. Synthesis, 2004, 15:2535 [19] Zhao Z., Wisnoski D.D., Wolkenberg S.E., Leister W.H., Wang Y., Lindsley C.W. Tetrahedron Lett., 2004, 45:4873 [20] Bhosale R.S., Sarda S.R., Ardhapure S.S., Jadhav W.N., Bhusare S.R., Pawar R.P. Tetrahedron Lett., 2005, 46:7183 [21] More S.V., Sastry M.N.V., Wang C.C., Yao C.F. Tetrahedron Lett., 2005, 46:6345 [22] Heravi M.M., Bakhtiari K., Tehrani M.H., Javadi N.M., Oskooie H.A. Arkivoc, 2006, 2006:16 [23] Hasaninejad A., Zare A., Mohammadizadeh M.R., Shekouhy M. Arkivoc, 2008, 2008:28 [24] Niknam K., Saberi D., Mohagheghnejad M. Molecul., 2009, 14:1915 [25] Bandyopadhyay D., Mukherjee S., Rodriguez R.R., Banik B.K. Molecul., 2010, 15:4207 [26] Darabi H.R., Aghapoor K., Mohsenzadeh F., Jalali M.R., Talebian S., Ebadi-Nia L., Khatamifar E., Aghaee A. Bull Korean Chem. Soc., 2011, 32:213 [27] Guo W.X., Jin H.L., Chen J.X., Chen F., Dinga J.C., Wu H.Y. J. Brazil. Chem. Soc., 2009, 6:1674 [28] Darabi H.R., Tahoori F., Aghapoor K., Taala F., Mohsenzadeh F. J. Brazil. Chem. Soc., 2008, 19:1646 [29] Hasaninejad A., Zareb A., Mohammadizadeh M.R., Karami Z. J. Iran Chem. Soc., 2009, 6:153 [30] Mahesh R., Dhar A.K., Tara Sasank T.V.N.V., Thirunavukkarasu S., Devadoss T. Chin. Chem. Lett., 2011, 22:389 [31] Dong F., Kai G., Zhenghao F., Xinli Z., Zuliang L. Catal. Commun., 2008, 9:317 [32] Hasaninejad A., Zare A., Shekouhy M., Moosavi-Zare A.R. E-J. Chem., 2009, 6:S247 [33] Islami M.R., Hassani Z. Arkivoc, 2008, 2008:280
Statistics Article View: 262 PDF Download: 192