Preparation and characterization of ionic liquid functionalized SBA-15 and its application in the synthesis of 2,3-dihydroquinazolinones
محورهای موضوعی : Iranian Journal of Catalysis
Ghodsi Mohammadi Ziarani
1
(Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran, P.O. Box 1993893973.)
Leila Seiedakbari
2
(Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran, P.O. Box 1993893973.)
Parisa Gholamzadeh
3
(Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran, P.O. Box 1993893973.)
Alireza Badiei
4
(School of Chemistry, College of Science, University of Tehran, Tehran, Iran.)
کلید واژه: One-pot reaction, Nano-catalyst, Quinazoline, SBA-15 functionalized ionic liquid, Isatoic anhydride,
چکیده مقاله :
N-Methyl-N</em>ʹ-propyltrimethoxysillylimidazolium chloride was prepared as ionic liquid (IL) containing silylating agent and then used for modification of the internal surface of SBA-15 to gain a heterogeneous ionic liquid catalyst. Subsequently, the obtained SBA-IL was characterized using various techniques, including SEM and TEM images, FT-IR, X-ray diffraction, TGA/DTA and BET analyses. It was found that the uniform SBA-15 particles, with a dimension of 400-800 nm, showed the decreasing in the pore volume, surface area, and pore diameter after modification process which is as a results of incorporating imidazole groups onto the pores of SBA-15. Afterward, catalytic activity of SBA-IL was investigated in the synthesis of 2,3-dihydroquinazolinones under solvent free condition.
[1] D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Science 279 (1998) 548-552.
[2] P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, Biocatal. Biotransform. 35 (2017) 131-150.
[3] P. Gholamzadeh, G. Mohammadi Ziarani, N. Lashgari, A. Badiei, A. Shayesteh, M. Jafari, J. Fluoresc. 26 (2016) 1857-1864.
[4] G. Mohammadi Ziarani, A. Badiei, M. Azizi, P. Gholamzadeh, L. Seyedakbari, Iran. J. Energy Environ. 2 (2013) 1-7.
[5] G. Mohammadi Ziarani, S. Ghorbi, P. Gholamzadeh, A. Badiei, Iran. J. Catal. 6 (2016) 229-235.
[6] G. Mohammadi Ziarani, P. Gholamzadeh, A. Badiei, S. Asadi, A.A. Soorki, J. Chil. Chem. Soc. 60 (2015) 2975-2978.
[7] G. Mohammadi Ziarani, N. Lashgari, A. Badiei, Current Org. Chem. 21 (2017) 674-687.
[8] G. Mohammadi Ziarani, R. Moradi, N. Lashgari, A. Badiei, A. Abolhassani Soorki, Polycycl. Aromat. Compd. (2016) DOI: 10.1080/10406638.2016.1154579.
[9] A.M. Liu, K. Hidajat, S. Kawi, D.Y. Zhao, Chem. Commun. (2000) 1145-1146.
[10] N. Lashgari, A. Badiei, G. Mohammadi Ziarani, F. Faridbod, Anal. Bioanal. Chem. 409 (2017) 3175–3185.
[11] N. Lashgari, A. Badiei, G. Mohammadi Ziarani, J. Phys. Chem. Solids 103 (2017) 238-248.
[12] M. Karimi, A. Badiei, N. Lashgari, G. Mohammadi Ziarani, J. Porous Mater. (2017) DOI: 10.1007/s10934-017-0427-9.
[13] T.P. Selvam, P.V. Kumar, Res. Pharm. 1 (2011) 1-21.
[14] R.S. Hunoor, B.R. Patil, D.S. Badiger, R.S. Vadavi, K.B. Gudasi, C.V. Magannavar, I.S. Muchandi, Chem. Pharm. Bull. 58 (2010) 712-716.
[15] E. Mikiciuk-Olasik, K. Baszczak-Światkiewiz, E. Żurek, U. Krajewska, M. Różalski, R. Kruszyński, T.J. Bartczak, Arch. Pharm. 337 (2004) 239-246.
[16] A. Kamal, E.V. Bharathi, J.S. Reddy, M.J. Ramaiah, D. Dastagiri, M.K. Reddy, A. Viswanath, T.L. Reddy, T.B. Shaik, S.N.C.V.L. Pushpavalli, M.P. Bhadra, Eur. J. Med. Chem. 46 (2011) 691-703.
[17] P.E. Petrides, Semin. Thromb. Hemost. 32 (2006) 399-408.
[18] S. Clissold, R. Beresford, Drugs 33 (1987) 478-502.
[19] M. Sharma, K. Chauhan, R. Shivahare, P. Vishwakarma, M.K. Suthar, A. Sharma, S. Gupta, J.K. Saxena, J. Lal, P. Chandra, J. Med. Chem. 56 (2013) 4374-4392.
[20] A. Iwashita, K. Hattori, H. Yamamoto, J. Ishida, Y. Kido, K. Kamijo, K. Murano, H. Miyake, T. Kinoshita, M. Warizaya, FEBS Lett. 579 (2005) 1389-1393.
[21] L. He, H. Li, J. Chen, X.-F. Wu, RSC Adv. 4 (2014) 12065-12077.
[22] S.Y. Afsar, G. Mohammadi Ziarani, H. Mollabagher, P. Gholamzadeh, A. Badiei, A.A. Soorki, J. Iran. Chem. Soc. 14 (2017) 577-583.
[23] D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120 (1998) 6024-6036.
[24] S. Hamoudi, A. El-Nemr, K. Belkacemi, J. Colloid Interface Sci. 343 (2010) 615-621.
[25] A. Badiei, H. Goldooz, G. Mohammadi Ziarani, Appl. Surf. Sci. 257 (2011) 4912-4918.
[26] T. Sasaki, C. Zhong, M. Tada, Y. Iwasawa, Chem. Commun. 19 (2005) 2506-2508.
[27] K. Niknam, A. Piran, Green Sustainable Chem. 3 (2013) 1-8.
[28] K. Niknam, A. Piran, Z. Karimi, J. Iran. Chem. Soc. 13 (2016) 859-871.
[29] M. Nouri Sefat, D. Saberi, K. Niknam, Catal. Lett. 141 (2011) 1713-1720.
[30] M. Baghernejad, K. Niknam, Internat. J. Chem. 4 (2012) 52-60.
[31] Y. Hu, S. Tang, L. Jiang, B. Zou, J. Yang, H. Huang, Process Biochem. 47 (2012) 2291-2299.
[32] B. Zou, Y. Hu, D. Yu, J. Xia, S. Tang, W. Liu, H. Huang, Biochem. Eng. J. 53 (2010) 150-153.
[33] G. Mohammadi Ziarani, L. Seyedakbari, S. Asadi, A. Badiei, M. Yadavi, Res. Chem. Intermed. 42 (2015) 499-509.
[34] G. Socrates, Infrared and Raman Characteristic Group Frequencies, John Wiley, 2004.
[35] H.R. Shaterian, A.R. Oveisi, M. Honarmand, Synth. Commun. 40 (2010) 1231-1242.
[36] A. Shaabani, A. Rahmati, J. Moghimirad, C.R. Chim. 11 (2008) 759-764.
[37] L. Wu, E-J. Chem. 9 (2012) 739-743.
[38] A. Moradi, R. Heydari, M.T. Maghsoodlou, Res. Chem. Intermed. 41 (2015) 7377-7391.
[39] A. Shaabani, A. Rahmati, J. Moghimirad, J. Heterocycl. Chem. 45 (2008) 1629-1632.
[40] H.R. Shaterian, N. Fahimi, K. Azizi, Res. Chem. Intermed. 40 (2014) 1879-1898.
