Synthesis of sulfamic acid functionalized-magnetic nanoparticles and application as a retrievable and efficient catalyst for the green synthesis of 1,4-dihydropyridine and 2,3-dihydroquinazoline derivatives

Subject Areas :

محمد علی  بداغی فرد ¹ (استادیار شیمی آلی، گروه شیمی، دانشکده علوم، دانشگاه اراک، اراک، ایران.)
الهام  علیمحمدی ² (کارشناس ارشد شیمی، دانشکده علوم، دانشگاه اراک، اراک، ایران)

Received: 2017-04-07 Accepted : 2017-12-09 Published : 2018-05-22

Keywords: Magnetite, green chemistry, Sulfamic acid, 1, 4-dihydropyridine, 2, 3-dihydroquinazoline,

Abstract :

1,4-Dihydropyridines and 2,3-dihydroquinazolines are heterocyclic compounds that have pharmacological and biological properties and most of their derivatives are produced in pharmaceutical industries. In this study preparation of bissulfamic acid-grafted on silica-coated nano-Fe3O4 particles (MNPs-TBSA), and their application as a retrievable heterogeneous acidic catalyst for the green synthesis of 1,4-Dihydropyridines and 2,3-dihydroquinazolines is probed. This nanocatalyst is easily separated from the reaction mixture with the assistance of an external magnetic field and reuse for several runs without deterioration in catalytic activity. The morphology, structure, and size of magnetic nanoparticles were characterized via SEM, XRD, EDS, FT-IR and TGA/DTA. Eco-friendly and non-toxic condition, high yield and purity of the desired products, short reaction time along with the ease of the workup procedure outline the advantages of these new methodologies over the earlier ones.

References:

[1] Atashkar, B.; Rostami, A.; Gholami, H.; Tahmasbi, B.; Res. Chem. Intermed. 41, 3675-3681, 2015.

[2] Han, L.; Choi, H.J.; Choi, S.J.; Liu, B.; Park, D.W.; Green Chem. 13, 1023-1028, 2011.

[3] Jagtap, S.R.; Raje, V.P.; Samant, S.D.; Bhanage, B.M.; J. Mol. Catal. A Chem. 266, 69-74, 2007.

[4] Sun, J.; Fujita, S.I.; Zhao, F.; Arai, M.; Green Chem. 6, 613-616, 2004.

[5] Rác, B.; Molnar, A.; Forgo, P.; Mohai, M.; Bertóti, I.; J. Mol. Catal. A Chem. 244, 46-57, 2006.

[6] Nasseri, M.A.; Sadeghzadeh, M.; J. Chem. Sci. 125, 537-544, 2013.

[7] Li, J.; Zhang, Y.; Han, D.; Gao, Q.; Li, C.; J. Mol. Catal. A Chem. 298, 31-35, 2009.

[8] Rostami, A.; Tahmasbi, B.; Abedi, F.; Shokri, Z.; J. Mol. Catal. A Chem. 378, 200-205, 2013.

[9] Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.M.; Chem. Rev. 111, 3036-3075, 2011.

[10] Safari, J.; Abedi-Jazini, Z.; Zarnegar, Z; Sadeghi, M.; J. Nanopart. Res. 17(12), 495, 2015.

[11] Rostamnia, S.; Amini, M.; J. Nanopart. Res. 16(5), 2405, 2014.

[12] Rostami, A.; Tahmasbi, B.; Gholami, H.; Taymorian, H.; Chin. Chem. Lett. 24, 211-214, 2013.

[13] Leng, Y.; Sato, K.; Shi, Y.; Li, J.G.; Ishigaki, T.; Yoshida, T.; Kamiya, H.; J. Phys. Chem. C 113, 16681-16685, 2009.

[14] Morel, A.L.; Nikitenko, S.I.; Gionnet, K.; Wattiaux, A.; Lai-Kee-Him, J.; Labrugere, C.; Chevalier, B.; Deleris, G.; Petibois, C.; Brisson, A.; Simonoff, M.; ACS Nano 2, 847-856, 2008.

[15] Reddy, G.M.; Shiradkar, M.; Chakravarthy, A.K.; Curr. Org. Chem., 11, 847-852, 2007.

[16] Inouye, M.; Mio, T.; Sumino, K.; E. J. Clin. Pharmacol. 56, 35-41, 2000.

[17] Beale, J.M.; Block, J.H.; “Textbook of Organic Medicinal and Pharmaceutical Chemistry – 12th Edition”, Wolters Kluwer-Lippincott Williams & Wilkins, China, 2011.

[18] Briede, J.; Daija, D.; Stivrina, M.; Duburs, G.; Cell Biochem. Funct. 17, 89-96, 1999.

[19] Bird, G.L.; Prach, A.T.; McMahon, A.D.; Forrest, J.A.; Mills, P.R.; Danesh, B.J.; J. Hepatol. 28, 194-198, 1998.

[20] Cihat, S.; Rahime, S.; Mini Rev. Med. Chem. 6, 747-755, 2006.

[21] Padia, J.K.; Field, M.; Hinton, J.; Meecham, K.; Pablo, J.; Pinnock, R.; Roth, B.D.; Singh, L.; Suman-Chauhan, N.; Trivedi, B.K.; Webdale, L., J. Med. Chem. 41, 1042–1049, 1998.

[22] Xia, Y.; Yang, Z.Y.; Hour, M.J.; Kuo, S.C.; Xia, P.; Bastow, K.F.; Nakanishi, Y.; Nampoothiri, P.; Hackl, T.; Hamel, E.; Lee, K.H., Bioorg. Med. Chem. Lett. 11, 1193–1196, 2011.

[23] Hour, M.J.; Huang, L.-J.; Kuo, S.C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.; J. Med. Chem. 43, 4479–4487, 2000.

[24] Can, K.; Ozmen, M.; Ersoz, M.; Colloids Surf. B Biointerfaces 71, 154-159, 2009.

[25] Stöber, W.; Fink, A.; Bohn, E.; J. colloid interface sci. 26, 62-69, 1968.

[26] Zeng, T.; Yang, L.; Hudson, R.; Song, G.; Moores, A.R.; Li, C.J.; Org. Lett. 13, 442-445, 2010.

[27] Bodaghifard, M.A.; Asadbegi, S.; Bahrami, Z.; J. Iran. Chem. Soc. 14, 365–376, 2017.

[28] Bodaghifard, M.A.; Faraki, Z.; Karimi, A.R.; Curr. Org. Chem. 20, 1648-1654, 2016.

[29] Buzzoni, R.; Bordiga, S.; Ricchiardi, G.; Spoto, G.; Zecchina, A.; J. Phys. Chem. 99, 11937-11951, 1995.

[30] Ghorbani-Choghamarani, A.; Darvishnejad, Z.; Tahmasbi, B.; Inorg. Chim. Acta., 435, 223-231, 2015.

[31] Hajjami, M.; Tahmasbi, B.; RSC Adv. 5, 59194-59203, 2015.

[32] Feng, G.; Hu, D.; Yang, L.; Cui, Y.; Cui, X.A.; Li, H.; Sep. Purif. Technol. 74, 253-260, 2010.

[33] Giri, J.; Thakurta, S.G.; Bellare, J.; Nigam, A.K.; Bahadur, D.; J. Magn. Magn. Mater. 293, 62-68, 2005.

[34] Marco-Contelles, J.; León, R.; de los Ríos, C.; Samadi, A.; Bartolini, M.; Andrisano, V.; Huertas, O.; Barril, X.; Luque, F.J.; Rodríguez-Franco, M.I.; López, B.; López, M.G.; García, A. G.; do Carmo Carreiras, M.; Villarroya, M.; J. Med. Chem. 52, 2724-2732, 2009.

[35] Marco-Contelles, J.; León, R.; de los Ríos, C.; Guglietta, A.; Terencio, J.; López, M.G.; García, A.G.; Villarroya, M.; J. Med. Chem. 49, 7607-7610, 2006.

[36] León, R.; de los Ríos, C.; Marco-Contelles, J.; López, M.G.; García, A.G.; Villarroya, M.; Eur. J. Med. Chem. 43, 668-674, 2008.

[37] Zonouz, A.M.; Moghani, D.; Synth. Commun. 41, 2152-2160, 2011.

[38] He, X.; Shang, Y.; Yu, Z.; Fang, M.; Zhou, Y.; Han, G.; Wu, F.; J. Org. Chem. 79, 8882-8888, 2014.

[39] Bodaghifard, M.A.; Mobinikhaledi, A.; Hamidinasab, M.; Synth. React. Inorg. Metal-Org. Nano-Met. Chem. 44, 567–571, 2014.

[40] Chen, J.; Su, W.; Wu, H.; Liu, M.; Jin, C., Green Chem, 9, 972–975, 2007.

[41] Chen, J.; Wu, D.; He, F.; Liu, M.; Wu, H.; Ding, J.; Su, W.; Tetrahedron Lett. 49, 3814–3818, 2008.

[42] Darvatkar, N.B.; Bhilare, S.V.; Deorukhkar, A.R.; Raut, D.G.; Salunkhe, M.M.; Green Chem. Lett. Rev. 3, 301-306, 2010.

[43] Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, Gh.; Mohammadi, A. A.; Tetrahedron Lett. 46, 6123–6126, 2005.

[[44]  Salehi,  P.;  Dabiri,  M.;  Baghbanzadeh,  M.; Bahramnejad,  M.;  Synth.  Commun.,  36, 2287–2292, 2006.

[45] Shaterian, H.R.; Oveisi, A.R.; Honarmand, M.; Synth. Commun. 40, 1231–1242, 2010.