Fe3O4@SiO2/BiPy2+2Cl– nanocomposite promoted rapid synthesis of Pyranopyrazole and Octahydroquinazoline derivatives
Subject Areas : PolymerSara Hosseini 1 , Ali Reza Kiasat 2 , Asadollah Farhadi 3
1 - Department of Chemistry, Khuzestan Science and Research Branch, Islamic Azad University, Ahvaz, Iran
Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
2 - Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
Chemistry Department, College of Science, Shahid Chamran University of Ahvaz, Ahvaz,Iran
3 - Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
Petroleum University of Technology, Faculty of Science, Ahvaz, Iran
Keywords:
Abstract :
Fe3O4@SiO2/bipyridinium chloride nanocomposite, Fe3O4@SiO2/BiPy+22Cl-, as a magnetically separable and recyclable heterogeneous catalyst was used for the one-pot synthesis of pyranopyrazole and octahydroquinazoline derivatives via multi-components cyclocondensation reaction under solvent free conditions. The catalyst was recovered by simple magnetic decantation and can be recycled several times with no significant loss of its catalytic activity. The results showed that the desired products were obtained with high efficiency, rapid, simple, and eco-friendly.
[1]. S. C. Kuo, L. J. Huang, H. Nakamura, J. Med. Chem., 27, 539 (1984).
[2]. J. L. Wang, D. Liu, Z. J. Zheng, S. Shan, X. Han, S. M. Srinivasula, C. Croce, E. S. Alnemri, Z.
Huang, Proc. Natl. Acad. Sci., U.S.A. 97, 7124 (2000).
[3]. M. E. A. Zaki, H. A. Soliman, O. A. Hiekal, A. E. Z. Rashad, Naturforsch., 61, 1 (2006).
[4]. D. Das, R. Banerjee, A. Mitra, J. Chem. Pharmaceut. Res., 6, 108 (2014).
[5]. R. Sakhuja, S. S. Panda, L. Khanna, S. Khurana, S.C. Jain, Bioorg. Med. Chem. Lett., 18, 5465
(2011).
[6]. M. Kidwai, S. Saxena, M. K. R. Khan, S. S. Thukral, Eur. J. Med. Chem., 40, 816 (2005).
[7]. S. Sikandar, A. F. Zahoor, J. Heterocyclic. Chem., 58, 685 (2021)
[8]. O. I. el-Sabbagh 1
, M. A. Shabaan, H. H. Kadry, E. Saad Al-Din, Eur. J. Med. Chem., 45, 5390
(2010).
[9]. S. Zheng, S. Zhong, Z. Chen, W. Chen, Q. Zhu, ACS Comb. Sci., 8, 475 (2016).
[10]. M. Ghobadi, M. Kargar Razi., R. Javahershenas, M. Kazemi, Synth. Commun., 51, 647 (2020).
[11]. K. K. Gangu, S. Maddila, S. N. Maddila, S .B. Jonnalagadda, RSC Advances, 7, 423 (2017).
[12]. B. Shaabani, H. Maleki, J. Rakhtshah, J. Organomet. Chem., 897, 139 (2019).
[13]. S. Hosseini, A.Kiasat, A Farhadi, Polycyclic Aromatic Compounds, 40, 1 (2019).
[14]. J. Etemad Gholtash, M. Farahi, RSC., 8, 40962 (2018).
[15]. S. Kantevari, R. Bantu, L. Nagarapu, ARKIVOC xvi., 3, 136 (2006).).
[16]. S. B. Kamble, A.S.Kumbhar, S.N. Jadhav, R. S. Salunkhe, Procedia Materials Science, 6,
1850 (2014
[17]. M. M. Candan, E. Kendi, M. Yarim, S. Sarac. M. Ertan, Anal. Sci., 17, 1023 (2001).
[18]. P. Movaheditabar, M. Javaherian, V. Nobakht, Appl. Organomet. Chem., 36, e6602 (2022).
[19]. N. N. Tonkikh, A. Strakovs, M. V. Petrova, Chem. Heterocycl. Compds., 2444, 43 (2004).
[20]. Z. Hassani, M. R. Islami, M. Bio. Med. Chem. Lett., 16, 4479 (2017).
[21]. S. N.Kirti, B. Shingate, S.S. Murlidhar, Tetrahedron Lett., 51, 3616 (2010).
[22]. O. Wolfgang, W. Fröstl, Tetrahedron Lett., 23, 361 (2006).
[23]. S. N. Kantevari, V. S. Vuppalapati, O. Biradar, D. L Nagarapu, J. Mol. Cata. A: Chem., 211,
649 (2007).
[24]. S. Hashemi-Uderji, M. Abdollahi- Alibeik, J. Iran. Chem. Soc., 15, 135 (2018).
[25]. K. S. Dalal, Y. A. Tayade, Y. B. Wagh, D.R. Trivedi, D. S. Dalal, B. L. Chaudhari, RSC Adv.,
6, 14868 (2016).
[26]. S. Hashemi-Uderji, M. Abdollahi-Alibeik, J. Iran. Chem. Soc., 15, 311 (2018).
[27]. H. Mecadon, M. R. Rohman, M. Rajbangshi, B. Myrboh, Tetrahedron Lett., 52, 2523 (2011).