Synthesis of Some Arylidene Heterobicyclic Compounds using Nano Al2O3-SO3H under Sonication Conditions

Subject Areas : Polymer

Noshin Seif ¹ (Department of Chemistry, Khuzestan Science and Research Branch, Islamic Azad University, Ahvaz, Iran. Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran.)
Asadollah Farhadi ² (Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran. Petroleum University of Technology, Faculty of Science, Ahvaz, Iran.)
Rashid Badri ³ (Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran.)
Ali Reza Kiasat ⁴ (Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran. Chemistry Department, College of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran.)

Received: 2021-11-21 Accepted : 2021-11-21 Published : 2021-10-01

Keywords:

Abstract :

The condensation of aromatic aldehydes, cyclopentanone and urea promoted by nano Al2O3-SO3H and HCl (aq) as heterogeneous and homogeneous catalysts, respectively, have been developed for the synthesis of some arylidene heterobicyclic compounds. In this synthesis, we have used two methods with sonication and thermal condition that have several advantages such as excellent yields and short reaction times. The ultrasonic device used in this study includes an ultrasonic bath equipped with a thermal system designed and built in our laboratory.

References:

[1]. M. K. Mohammadi, S. J. Saghanezhad, N. Razzaghi-asl, Bull. Chem. Soc. Ethiop, 31,
535 (2017).
[2]. N. Nakamichi, Y. Kawashita, M. Hayashi, Synthesis, 1015 (2004).
[3]. K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg,
B.C. Oreilly, J. Med. Chem. 34, 806 (1991).
[4]. A. D. Patil, N. V. Kumar, W. C. Kokke, M. F. Bean, A. J. Freyer, C. D. Brosse, S.
Mai, A. Truneh, B. Carte, J. Org. Chem, 60, 1182 (1995).
[5]. H. I. EI-Subbagh, S. M. Abu-Zaid, M. A. Mahran, F. A. Badria, A. M. Al-Obaid, J.
Med. Chem, 43, 2915 (2000).

[6]. C. O. Kappe, Eur. J. Med. Chem, 35, 1043 (2000).
[7]. M. Ashok, B. S. Holla, N. S. Kumari, Eur. J. Med. Chem, 42, 380 (2007).
[8]. P. Biginelli, Gazz. Chim. Ital, 23, 360 (1893).
[9]. A. R. Hajipour, Y. Ghayeb, N. Sheikhan, A. E. Ruoho,Synth. Commun,41, 2226
(2011).
[10]. M. T. Maghsoodlou, R. Heydari,M. Lashkari, F. Mohamadpour, Indian J. Chem, 56B,
160 (2017).
[11]. A. Farhadi, M. A. Takassi, L. Hejazi, Z.Naturforsh, 68b, 51 (2013).
[12]. A. Farhadi, J. Noei, R. Haji Aliyari, M. Albakhtiyari, M. A. Takassi, Res. Chem.
Intermed, 42, 1401 (2015).
[13]. H. Kiyani, M. Ghiasi, J. Res. Chem. Intermed, 41,6635 (2015).
[14]. M. Ould M’hamed, A. G. Alshammari, O. M. Lemine, Appl. Sci, 6, 431 (2016).
[15]. Y. T. Reddy,R. P. Narsimha, B. S. Kumar, G. V. P. Rao, B. Rajitha,Indian J. Chem,
44B, 1304 (2005).
[16]. A. Farhadi, M. A. Takassi, L. Hejazi, Iran. Chem. Commun, 5, 35 (2017).
[17]. Y. L. Zhu, S. L. Huang, Y. J. Pan,Eur. J. Org. Chem, 11, 2354 (2005).
[18]. M. Mehrabi, A. Farhadi, A. R. Kiassat,Int. J. Org. Chem, 3, 240 (2017).
[19]. A. P. Martins. Marcos, P. Frizzo. Clarissa, N. Moreira. Dayse, L. Buriol, P. Machado,
Chem. Rev, 109, 4140 (2009).
[20]. T. J. Mason, L. Paniwnyk, J. P.Lorimer, Ultrason. Sonochem, 3, S253 (1996).
[21]. J. T. Li, J. F. Han, J. H. Yang, T. S.Li, Ultrason. Sonochem, 10, 119 (2003).
[22]. H. R. Memarian, A.Farhadi,Ultrason. Sonochem, 15, 1015 (2008).
[23]. H. R. Memarian, M. Soleymani, Ultrason. Sonochem, 18, 745 (2011).
[24]. M. Kalhor, Z. Zarnegar, RSC Adv, 9, 19333 (2019).
[25]. A. Bamoniri, N. Yaghmaeiyan-Mahabadi, Sci. Iran. C, 25, 1344 (2018).
[26]. L. Chen, J. Zhao, S. F. Yin, C. T. Au, RSC. Adv, 3, 3799 (2013).
[27]. A. Habibi, E. Ghanbari, I.Yavari, J. Iran. Chem. Soc. 16, 2519, (2019).
[28]. H. Faroughi Niya, N. Hazeri, M. T. Maghsoodlou, Appl. Organometal. Chem,
e5457, 1 (2020)

[29]. S. Sajjadifar, I. Amini, |G. Mansouri, S. Alimohammadi, Eurasian Chem. Commun.
2, 626 (2020).
[30]. A.Farhadi, M. A.Takassi, M.Enjilzadeh, F.Davod, J. Appl. Chem. Res, 12, 48
(2018).
[31]. A. R. Kiassat, S. Noorizadeh, M. Ghahremani, S. J. Saghanejad, J. Mol. Struc, 1036, 216-225 (((2013).
[32]. K. Aswin, M. Ghashang, S. S. Mansoor,Iran. J. Catal. 5, 175 (2015).
[33]. O. O. Ajani, R. I. Ituen, A. Falomo, Pak. J. Sci. Ind. Res. Ser. A: Phys. Sci, 54, 59
(2011).
[34]. A. Amoozadeh, S. Rahmani, F. Nemati, Heterocycl Commun, 19, 69 (2013).