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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

One Pot Synthesis of Benzothiazole Derivatives by Nano Silica-based Complex in an Aqueous Medium

Author(s): Hassan Yari, Ghasem Rezanejade Bardajee, Rahebeh Amiri Dehkharghani* and Niloufar Akbarzadeh Torbati

Volume 20, Issue 3, 2023

Published on: 24 October, 2022

Page: [265 - 275] Pages: 11

DOI: 10.2174/1570178619666220922092029

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Abstract

We successfully synthesized novel silica-supported Ni (II)-PLP-ONNO Schiff base/SBA- 15 complex, as a mesoporous catalyst, whose characterization was determined using X-ray diffraction analysis, Fourier-transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, inductively coupled plasma-atomic emission spectroscopy, nitrogen adsorption desorption isotherms (BET-EDX) and (BET-BJH), and thermo-gravimetric analysis. A fabricated catalyst was employed for facile and efficient, one-pot production of various benzothiazole heterocycles by cyclocondensation reactions of 2-amionthiophenol and benzaldehyde compounds under green and mild conditions with good to excellent yields. The prepared nano catalyst can offer high stability, excellent activity, easy separation, and reusability, as well as environmentally friendly, compared to its homogeneous compounds.

Keywords: Nanocatalyst, nickel complex, pyridoxal phosphate schiff base, benzothiazole, heterocycles, SBA-15.

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[1]
Sharma, A.S.; Sharma, V.S.; Kaur, H.; Varma, R.S. Green Chem., 2020, 22(18), 5902-5936.
[http://dx.doi.org/10.1039/D0GC01927E]
[2]
Jeevanandam, J.; Barhoum, A.; Chan, Y.S.; Dufresne, A.; Danquah, M.K. Beilstein J. Nanotechnol., 2018, 9, 1050-1074.
[http://dx.doi.org/10.3762/bjnano.9.98] [PMID: 29719757]
[3]
Somwanshi, S.B.; Somvanshi, S.B.; Kharat, P.B. J. Phys. Conf. Ser., 2020, 1644(1), 012046.
[http://dx.doi.org/10.1088/1742-6596/1644/1/012046]
[4]
ALOthman, Z. Materials (Basel), 2012, 5(12), 2874-2902.
[http://dx.doi.org/10.3390/ma5122874]
[5]
Chircov, C.; Spoială, A.; Păun, C.; Crăciun, L.; Ficai, D.; Ficai, A.; Andronescu, E.; Turculeƫ, Ș.C. Molecules, 2020, 25(17), 3814.
[http://dx.doi.org/10.3390/molecules25173814] [PMID: 32825791]
[6]
da Silva, C.M. SN. Applied Sciences, 2019, 1, 654.
[7]
Hussein, A.H.; Nahas, H.; Jahjah, M.; Srour, M.; Jahjah, R.; Duget, N.; Lemaire, M.; Naoufal, D. Int. J. Org. Chem. (Irvine), 2018, 8(1), 16-40.
[http://dx.doi.org/10.4236/ijoc.2018.81002]
[8]
Morsi, R.E.; Mohamed, R.S. R. Soc. Open Sci., 2018, 5(3), 172021.
[http://dx.doi.org/10.1098/rsos.172021] [PMID: 29657800]
[9]
Thielemann, J.P.; Girgsdies, F.; Schlögl, R.; Hess, C. Beilstein J. Nanotechnol., 2011, 2, 110-118.
[http://dx.doi.org/10.3762/bjnano.2.13] [PMID: 21977421]
[10]
Verma, P.; Kuwahara, Y.; Mori, K.; Raja, R.; Yamashita, H. Nanoscale, 2020, 12(21), 11333-11363.
[http://dx.doi.org/10.1039/D0NR00732C] [PMID: 32285073]
[11]
Yamamoto, E.; Mori, S.; Shimojima, A.; Wada, H.; Kuroda, K. Nanoscale, 2017, 9(7), 2464-2470.
[http://dx.doi.org/10.1039/C6NR07416B] [PMID: 27824195]
[12]
Amin, M.H. Catalysts, 2020, 10(1), 51.
[http://dx.doi.org/10.3390/catal10010051]
[13]
Barczak, M. J. Solid State Chem., 2018, 258, 232-242.
[http://dx.doi.org/10.1016/j.jssc.2017.10.006]
[14]
Bharti, C.; Gulati, N.; Nagaich, U.; Pal, A.K. Int. J. Pharm. Investig., 2015, 5(3), 124-133.
[http://dx.doi.org/10.4103/2230-973X.160844] [PMID: 26258053]
[15]
Chaudhary, V.; Sweta Chin. J. Chem. Eng., 2018, 26(6), 1300-1306.
[http://dx.doi.org/10.1016/j.cjche.2018.01.025]
[16]
Chaudhary, V.; Sharma, S. J. Porous Mater., 2017, 24(3), 741-749.
[http://dx.doi.org/10.1007/s10934-016-0311-z]
[17]
Davarpanah, J.; Elahi, S.; Rezaee, P. J. Porous Mater., 2018, 25(1), 161-170.
[http://dx.doi.org/10.1007/s10934-017-0429-7]
[18]
Feng, Y.; Panwar, N.; Tng, D.J.H.; Tjin, S.C.; Wang, K.; Yong, K.T. Coord. Chem. Rev., 2016, 319, 86-109.
[http://dx.doi.org/10.1016/j.ccr.2016.04.019]
[19]
Hoang, V.T.; Huang, Q.; Eić, M.; Do, T.O.; Kaliaguine, S. Langmuir, 2005, 21(5), 2051-2057.
[http://dx.doi.org/10.1021/la048349d] [PMID: 15723510]
[20]
Huirache-Acuña, R.; Nava, R.; Peza-Ledesma, C.; Lara-Romero, J.; Alonso-Núez, G.; Pawelec, B.; Rivera-Muñoz, E. Materials (Basel), 2013, 6(9), 4139-4167.
[http://dx.doi.org/10.3390/ma6094139] [PMID: 28788323]
[21]
Magyari, J.; Barta Holló, B.; Vojinović-Ješić, L.S.; Radanović, M.M.; Armaković, S.; Armaković, S.J.; Molnár, J.; Kincses, A.; Gajdács, M.; Spengler, G.; Mészáros Szécsényi, K. New J. Chem., 2018, 42(8), 5834-5843.
[http://dx.doi.org/10.1039/C8NJ00357B]
[22]
Abu-Dief, A.M.; Mohamed, I.M.A. Beni. Suef Univ. J. Basic Appl. Sci., 2015, 4(2), 119-133.
[PMID: 32289037]
[23]
Bhowmick, A.; Nath, B.; Moim, M. Coordination Complexes of Transition Metals and Schiff Base with Potent Medicinal Activity., 2019, 9, 109-114.
[24]
Ghanghas, P.; Choudhary, A.; Kumar, D.; Poonia, K. Inorg. Chem. Commun., 2021, 130, 108710.
[http://dx.doi.org/10.1016/j.inoche.2021.108710]
[25]
Gupta, K.C.; Sutar, A.K. Coord. Chem. Rev., 2008, 252(12-14), 1420-1450.
[http://dx.doi.org/10.1016/j.ccr.2007.09.005]
[26]
Kajal, A.; Bala, S.; Kamboj, S.; Sharma, N.; Saini, V. J. Catal., 2013, 2013, 893512.
[27]
Esmaielzadeh, S.; Zarenezhad, E. Acta Chim. Slov., 2018, 65(2), 416-428.
[http://dx.doi.org/10.17344/acsi.2018.4159] [PMID: 29993095]
[28]
Zhang, J.; Xu, L.; Wong, W.Y. Coord. Chem. Rev., 2018, 355, 180-198.
[http://dx.doi.org/10.1016/j.ccr.2017.08.007]
[29]
Amadasi, A.; Bertoldi, M.; Contestabile, R.; Bettati, S.; Cellini, B.; Luigi di Salvo, M.; Borri-Voltattorni, C.; Bossa, F.; Mozzarelli, A. Curr. Med. Chem., 2007, 14(12), 1291-1324.
[http://dx.doi.org/10.2174/092986707780597899] [PMID: 17504214]
[30]
Du, Y.L.; Ryan, K.S. Nat. Prod. Rep., 2019, 36(3), 430-457.
[http://dx.doi.org/10.1039/C8NP00049B] [PMID: 30183796]
[31]
Fleischman, N.M.; Das, D.; Kumar, A.; Xu, Q.; Chiu, H.J.; Jaroszewski, L.; Knuth, M.W.; Klock, H.E.; Miller, M.D.; Elsliger, M.A.; Godzik, A.; Lesley, S.A.; Deacon, A.M.; Wilson, I.A.; Toney, M.D. Protein Sci., 2014, 23(8), 1060-1076.
[http://dx.doi.org/10.1002/pro.2493] [PMID: 24888348]
[32]
Parra, M.; Stahl, S.; Hellmann, H. Cells, 2018, 7(7), 84.
[http://dx.doi.org/10.3390/cells7070084] [PMID: 30037155]
[33]
Rocha, J.F.; Pina, A.F.; Sousa, S.F.; Cerqueira, N.M.F.S.A. Catal. Sci. Technol., 2019, 9(18), 4864-4876.
[http://dx.doi.org/10.1039/C9CY01210A]
[34]
Björk, E.M. J. Chem. Educ., 2017, 94(1), 91-94.
[http://dx.doi.org/10.1021/acs.jchemed.5b01033]
[35]
Luan, Z.; Xu, J.; He, H.; Klinowski, J.; Kevan, L. J. Phys. Chem., 1996, 100(50), 19595-19602.
[http://dx.doi.org/10.1021/jp962353j]
[36]
Prajapati, N.P.; Vekariya, R.H.; Borad, M.A.; Patel, H.D. RSC Advances, 2014, 4(104), 60176-60208.
[http://dx.doi.org/10.1039/C4RA07437H]
[37]
Küçükbay, F.Z.; Buğday, N.; Küçükbay, H.; Tanc, M.; Supuran, C.T. J. Enzyme Inhib. Med. Chem., 2016, 31(6), 1221-1225.
[http://dx.doi.org/10.3109/14756366.2015.1114931] [PMID: 26598927]
[38]
Irfan, A.; Batool, F.; Zahra Naqvi, S.A.; Islam, A.; Osman, S.M.; Nocentini, A.; Alissa, S.A.; Supuran, C.T. J. Enzyme Inhib. Med. Chem., 2020, 35(1), 265-279.
[http://dx.doi.org/10.1080/14756366.2019.1698036] [PMID: 31790602]
[39]
Kosmulski, M.; Mączka, E.; Ruchomski, L. Colloids and Interfaces, 2018, 2(4), 59.
[http://dx.doi.org/10.3390/colloids2040059]
[40]
Uremis, N.; Uremis, M.M.; Tolun, F.I.; Ceylan, M.; Doganer, A.; Kurt, A.H. Anticancer Res., 2017, 37(11), 6381-6389.
[PMID: 29061823]
[41]
Chen, G.F.; Jia, H.M.; Zhang, L.Y.; Chen, B.H.; Li, J.T. Ultrason. Sonochem., 2013, 20(2), 627-632.
[http://dx.doi.org/10.1016/j.ultsonch.2012.09.010] [PMID: 23122553]
[42]
Gao, X.; Liu, J.; Zuo, X.; Feng, X.; Gao, Y. Molecules, 2020, 25(7), 1675.
[http://dx.doi.org/10.3390/molecules25071675] [PMID: 32260500]
[43]
Gunathilake, C.; Kalpage, C.; Kadanapitiye, M.; Dassanayake, R.S.; Manchanda, A.S.; Gangoda, M. J. Compos. Sci., 2019, 3(3), 77.
[http://dx.doi.org/10.3390/jcs3030077]
[44]
Liu, S.; Chen, R.; Guo, X.; Yang, H.; Deng, G. Green Chem., 2012, 2012(6), 1577-1580.
[45]
Malik, M.A.; Dar, O.A.; Gull, P.; Wani, M.Y.; Hashmi, A.A. MedChemComm, 2018, 9(3), 409-436.
[http://dx.doi.org/10.1039/C7MD00526A] [PMID: 30108933]
[46]
Zhilitskaya, L.V.; Shainyan, B.A.; Yarosh, N.O. Molecules, 2021, 26(8), 2190.
[http://dx.doi.org/10.3390/molecules26082190] [PMID: 33920281]
[47]
Zhao, D.; Feng, J.; Huo, Q.; Melosh, N.; Fredrickson, G.H.; Chmelka, B.F.; Stucky, G.D. Science, 1998, 279(5350), 548-552.
[http://dx.doi.org/10.1126/science.279.5350.548] [PMID: 9438845]
[48]
Chisem, I.C.; Rafelt, J.; Chisem, J.; Clark, J.H.; Macquarrie, D.; Shieh, T.; Jachuck, R.; Ramshaw, C.; Scott, K. Chem. Commun., 1998, 1998(18), 853-860.
[49]
Kumar, Y.; Ila, H. Org. Lett., 2019, 21(19), 7863-7867.
[http://dx.doi.org/10.1021/acs.orglett.9b02855] [PMID: 31525060]
[50]
More, M.S.; Joshi, P.G.; Mishra, Y.K.; Khanna, P.K. Mater. Today Chem., 2019, 14, 100195.
[http://dx.doi.org/10.1016/j.mtchem.2019.100195] [PMID: 32289101]
[51]
Ruchomski, L.; Pikus, S.; Pikula, T.; Mączka, E.; Kosmulski, M. Colloids Surf. A Physicochem. Eng. Asp., 2020, 599, 124922.
[http://dx.doi.org/10.1016/j.colsurfa.2020.124922]
[52]
Bochatay, V.N.; Boissarie, P.J.; Murphy, J.A.; Suckling, C.J.; Lang, S. J. Org. Chem., 2013, 78(4), 1471-1477.
[http://dx.doi.org/10.1021/jo302544d] [PMID: 23316812]
[53]
Cheng, Y.; Yang, J.; Qu, Y.; Li, P. Org. Lett., 2012, 14(1), 98-101.
[http://dx.doi.org/10.1021/ol2028866] [PMID: 22146071]
[54]
Kumar, P. J. Heterocycl. Chem., 2012, 49(5), 1243-1249.
[http://dx.doi.org/10.1002/jhet.962]
[55]
Nguyen, L.A.; Ngo, Q.A.; Retailleau, P.; Nguyen, T.B. Green Chem., 2017, 19(18), 4289-4293.
[http://dx.doi.org/10.1039/C7GC01825H]
[56]
Ranjit, S.; Liu, X. Chemistry, 2011, 17(4), 1105-1108.
[http://dx.doi.org/10.1002/chem.201002787] [PMID: 21243674]
[57]
Sung, G.H.; Lee, I.H.; Kim, B.R.; Shin, D.S.; Kim, J.J.; Lee, S.G.; Yoon, Y.J. Tetrahedron, 2013, 69(17), 3530-3535.
[http://dx.doi.org/10.1016/j.tet.2013.02.093]
[58]
Teo, Y.C.; Riduan, S.N.; Zhang, Y. Green Chem., 2013, 15(9), 2365-2368.
[http://dx.doi.org/10.1039/c3gc41027g]
[59]
Tian, Q.; Luo, W.; Gan, Z.; Li, D.; Dai, Z.; Wang, H.; Wang, X.; Yuan, J. Molecules, 2019, 24(1), 174.
[http://dx.doi.org/10.3390/molecules24010174] [PMID: 30621218]
[60]
Yang, X.L.; Xu, C.M.; Lin, S.M.; Chen, J.X.; Ding, J.C.; Wu, H.Y.; Su, W.K. J. Braz. Chem. Soc., 2010, 21(1), 37-42.
[http://dx.doi.org/10.1590/S0103-50532010000100007]

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