A Novel Cobalt Organic-Inorganic Hybrid Magnetic Nanocatalyst for Convenient Four-Component Synthesis of 3,4-Dihydropyridones

محورهای موضوعی : Iranian Journal of Catalysis

Maryam Barazandehdoust ¹ (Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran)
Manouchehr Mamaghani ² (Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran |Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran)
Hassan Kefayati ³ (Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran)

تاریخ دریافت : 1401/04/25 تاریخ پذیرش : 1401/08/23 تاریخ انتشار : 1401/10/10

کلید واژه: One-pot, 3, Nanocatalyst, 4-Dihydropyridone, Four-component, Meldrumʼs acid, γ-Fe2O3@HAp/Co(II),

چکیده مقاله :

Densely functionalized 3,4-dihydropyridones were synthesized by a four-component reaction of Meldrumʼs acid, ethyl acetoacetate, ammonium acetate, and proper aromatic aldehydes in the presence of novel organic-inorganic cobalt incorporated magnetic nanocatalyst (γ-Fe2O3@HAp/Co(II)) using ethanol as a green solvent at reflux condition. This new synthetic method provided the target compounds in a high yield (70-95%) and lower reaction time (20-75 min). The protocol benefits from the high purity of the products, environmentally friendly, milder reaction conditions, recyclability of the catalyst, and facile workup procedure. The structure of the synthesized novel nanocatalyst was confirmed by FT-IR, XRD, FSEM, TEM, EDS, and TGA analyses. The catalyst was used in eight cycles without any notable variation in catalytic activities.

منابع و مأخذ:

[1] E. Ruijter, R. Scheffelaar, R. V. A. Orru, Angew 50 (2011) 6234-6246.

[2] I. V. Magedov, A. Kornienko, Chem. Heterocycl. Compd. 48 (2012) 33-38.

[3] R. Dua, S. Shrivastava, S. K. Sonwane, S. K. Srivastava, Adv. Biol. Res. 5 (2011) 120-144.

[4] H. S. Hilal, M. S. Ali-Shtayeh, R. Arafat, T. Al-Tel, W. Voelter, A. Barakat, Eur. J. Med. Chem. 41 (2006) 1017-1024.

[5] R. Budriesi, A. Bisi, P. Ioan, A. Rampa, S. Gobbi, F. Belluti, L. Piazzi, P. Valenti, A. Chiarini, Bioorg. Med. Chem. 13(2005), 3423-3430.

[6] L. Navidpour, H. Shafaroodi, R. Miri, A. R. Dehpour, A. Shafiee, Farmaco 59 (2004) 261-269.

[7] I. Adachi, T. Yamamori, Y. Hiramatsu, K. Sakai, S-I. Mihara, M. Kawakami, M. Masui, O. Uno, M. Ueda, Chem. Pharm. Bull. 36 (1988) 4389-4402.

[8] R. Preston Mason, Cerebrovasc. Dis. 16 (2003) 11-17.

[9] S. Yamagishi, T. Matsui, K. Nakamura, Med. Hypotheses 68 (2007) 1096-1098.

[10] G. Duburs, B. Vigante, A. Plotniece, A. Krauze, A. Sobolevs, J. Briede, V. KluṦa, A. Velena, Med. Chem. 26(2008) 68-70.

[11] A. Hantzsch, Jus. Lie. Ann. Chim. 215 (1882) 1-82.

[12] N. C. Desai, A. M. Dodiya, N. R. Shihory, Med. Chem. Res. 21 (2012) 2579-2586.

[13] M. Nuchter, B. Ondruschka, A. Jungnickel, U. Muller, J. Phys. Org. Chem. 13(2000) 579-586.

[14] H. Rodriguez, O. Reyes, M. Suarez, H. Garay, R. Perez, J. Cruz, Y. Verdecia, N. Martin, C. Seoane, Tetrahedron lett. 43 (2002) 439-441.

[15] H. Rodriguez, M. Suarez, R. Perez, A. Petit, A. Loupy, Tetrahedron lett. 44 (2003) 3709-3712.

[16] G. Mohammadi Ziarani, S. Mousavi, N. Lashgari, A. Badiei, J. Chem. Sci. 125 (2013) 1359-1364.

[17] A. Modarres Hakimi, N. Lashgari, S. Mahernia, G. Mohammadi Ziarani, M. Amanlou, Res Pharm Sci. 12 (2017) 353-363

[18] N. A. Hamdy, A. M. Gamal-Eldeen, Eur. J. Med. Chem. 44(2009) 4547-4556.

[19] G. Mohammadi Ziarani, A. R. Badiei, Y. Khaniania, M. Haddadpour, Iran. J. Chem. Chem. Eng. 29 (2010) 1-10.

[20] G. Mohammadi Ziarani, A. Badiei, F. Shahjafari, T. Pourjafar, S. Afr. J. Chem. 65 (2012) 10-13.

[21] G. Mohammadi Ziarani, A. Abbasi, A. Badiei, Z. Aslani, Eur. J. Chem. 8(2011)293-299.

[22] N. Lashgari, G. Mohammadi Ziarani, A. Badiei, P. Gholamzadeh, Eur. J. Chem. 3 (2012) 310-313.

[23] L. Ma’mani, M. Sheykhan, A. Heydari, M. Faraji, Y. Yamini, Appl. Catal. A-Gen. 377 (2010) 64-69.

[24] M. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A Ramazani, A Shafiee, J. Mol. Catal. A 359 (2012) 74-80.

[25] M. Sheykhan, M. Mohammadquli, A. Heydari, J. Mol. Struct. 1027 (2012) 156-161.

[26] M. Mohsenimehr, M. Mamaghani, F. Shirini, M. Sheykhan, F. Azimian Moghaddam, Chinese Chem. Lett. 25 (2014) 1387-1391.

[27] L. Ma’mani, M. Sheykhan, A. Heydari, Appl. Catal. A-Gen. 395 (2011) 34-38.

[28] M. Sheykhan, L. Ma’mani, A. Ebrahimi, A. Heydari, J. Mol. Catal. A-Chem. 335 (2011) 253-261.

[29] M. Barazandehdoust, M. Mamaghani, H. Kefayati, React. Kinet. Mech. Cat. 129 (2020) 1007-1026.

[30] Bd. Cullity, Elements of X-ray diffraction. Third Edition Addison-Wesley Publishing Company, London (1956).

[31] S. Thomas, K. Joseph, S. K. Malhotra, K. Goda, M. S. Sreekala, Polymer composites, nanocomposites. Wiley-VCH Weinheim 2 (2013).

[32] E. Ruiz, H. Rodríguez, J. Coro, E. Salfrán, M. Suárez, R. Martínez-Alvarez, N. Martín, Ultrason. Sonochem. 18 (2011) 32-36.