Synthesis of densely functionalized chromenes using a magnetic recoverable ionic liquid as the catalyst

Document Type : Articles

Authors

1 Department of Chemistry, Faculty of Sciences, Islamic Azad University, Rasht Branch, Rasht, Iran

2 Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran

Abstract

In the present study, robust, versatile and straightforward strategy for the diversity-oriented convergent synthesis of a vast range of highly functionalized and biologically effective chromenes is introduced with the reaction of malononitrile, dimedone/cyclohexadione/4-hydroxycoumarin and benzaldehydes in the presence of [γ-Fe2O3@HAp-Si(CH2)3BF4@DMIM] as the catalyst. The structures of all the newly synthesized products were characterized by spectroscopic (FT-IR, 1H NMR, 13C NMR) and elemental analyses. This method benefits from several advantages such as using easily recoverable magnetic nanocatalyst, simple workup, short reaction time and excellent yields. The prepared nanoparticles were fully characterized by various spectroscopic, thermal and magnetic analyses. The catalyst exhibited good reusability feature and no loss of activity was observed even after 8 successive runs.

Graphical Abstract

Synthesis of densely functionalized chromenes using a magnetic recoverable ionic liquid as the catalyst

Highlights

• Novel imidazolium-based ionic liquids supported on hydroxyapatite encapsulated γ-Fe2O3 nanocatalyst [γ-Fe2O3@HAp-Si(CH2)3BF4@DMIM] was synthesized.

• The synthesized nanocatalyst was applied in an environmentally benign approach for the straightforward and practical synthesis of a wide range of densely functionalized chromenes.

• The catalyst was recycled and reused in 8 consecutive runs with negligible decrease in activity.

Keywords

References

[1] R. Pratap, V. Ji Ram, Chem. Rev. 114 (2014) 10476-10526.
[2] M. Gold, Y. Mujahid, Kh. Ahmed, H. Kostrhunova, J. Kasparkova, V. Brabec, B. Biersack and R. Schobert, J.Biol. Inorg. Chem. 24 (2019) 647-657.
[3] K. Y. Lum, A. R. Carroll, M. G. Ekins, S. Read, Z. Haq, I. Tietjen, J. S. John and R. A. Davis, Mar. Drugs. 17 (2019) 26-34.
[4] J. Chen, J. Cho, T. Hwang and I. Chen, J. Nat. Prod. 71 (2008) 71-75.
[5] W. Gregor, G. Grabner, C. Adelwohrer, T. Rosenau and L. Gille, J. Org. Chem. 70 (2005) 3472-3483.
[6] C. Bruhlmann, F. Ooms, P. Carrupt, B. Testa, M. Catto, F. Leonetti, C. Altomare and A. Cartti, J. Med. Chem. 44 (2001) 3195-3198.
[7] A. Aminkhani, M. Talati, R. Sharifi, F. Chalabian and F. Katouzian, J. Heterocycl. Chem. 56 (2019) 1812-1819.
[8] N. D. Thanh, D. Son Hai, V. Th. Ngoc Bich, Ph. Th. Thu Hien, N. Th. Ky. Duyen, N. Th. Mai, T. Th. Dung, V. N. Toan, H. Th. Kim Van, L. H. Dang, D. N. Toan and T. Th. Thanh Van,Eur. J. Med. Chem. 167 (2019) 454-471.
[9] F. F. Alblewi, R. M. Okasha, Z. M. Hritani, H. M. Mohamed, M. A.A. El-Nassag, A. H. Halawa, A. Mora, A. M. Fouda, M. A. Assiri, Al-A. M. Al-Dies, T. H. Afifi and A. M. El-Agrody, Bioorg. Chem. 87 (2019) 560-571.
[10] O. J. Jesumoroti, D. Faridoon, M. Mnkandhla, H. C. H. Isaacs and R. Klein, Med. Chem. Commun. 10 (2019) 80-88. 
[11] A. Yu. Sidorenko, A. V. Kravtsova, A. Aho, I. Heinmaa, J. Wärnå, H. Pazniak, K. P. Volcho, N. F. Salakhutdinov, D. Yu. Murzin and V.E. Agabekov, J. Catal. 374 (2019) 360-377.
[12] A. Smuszkiewicz, J. L´opez-Sanz, I. Sobczak, R. M. Martin-Aranda, M. Ziolek and E. Perez-Mayoral, Catal. Today. 325 (2019) 47-52.
[13] J. Balou, M. A. Khalilzadeh and D. Zareyee,Sci. Rep. 9 (2019) 3605-3613.
[14] Y. Pourshojaei, F. Zolala, Kh. Eskandari, M. Talebi, L. Morsali, M. Amiri, A. Khodadadi, R. Shamsimeymandi, E. Faghih-Mirzaei, A. Asadipour, J. Nanosci. Nanotechnol. 20 (2020) 3206-3216.
[15] J. Albadi, H. Samimi, A. R. Momeni, Chem. Methodol. 4 (2020) 565-571.
[16] R. Mohammadipour, A. Bamoniri, B. B. F. Mirjalili, Sci. Iran. 27 (2020) 1216-1225.
[17] A. Rimus Liandi, R. Tri Yunarti, M. Fajri Nurmawan, A. Herry Cahayana, Mater Today 22 (2020) 193-198.
[18] N. Monadi, H. Davoodi, M. Aghajani, React. Kinet. Mech. Catal. 129 (2020) 659-677.
[19] M. A. Bodaghifard, Z. Mozaffari, Z. Faraki, Iran. J. Catal. 10 (2) (2020) 101-110.
[20] M. Pourghasemi, F. Shirini, M. Alinia-Asli, M. A. Rezvani, J. Nanosci. Nanotechnol. 20 (2020) 973-982.
[21] M. Anvari Gharabaghlou, N. Shadjou, A. Poursattar Marjani, Appl. Organomet. Chem. 2020; e 5868.
[22] H. Naeimi, S. Mohammadi, ChemistrySelect 5 (2020) 2627-2633.
[23] A. R. Moosavi-Zare, H. Afshar-Hezarkhani, Iran. J. Catal. 10 (2) (2020) 119-126.
[24] P. Jahanshahi, M. Mamaghani, F. Haghbin, R. Hossein nia and M. Rassa, J. Mol. Struct. 1155 (2018) 520-529.
[25] M. Mohsenimehr, M. Mamaghani, F. Shirini, M. Sheykhan, S. Abbaspour and L.S. Sabet,J. Chem. Sci. 127 (2015) 1895-1904.
[26] M. Mamaghani, F. Shirini, M. Sheykhan and M. Mohsenimehr, RSC Adv. 5 (2015) 44524-44529.
[27] P. Farokhian, M. Mamaghani, N. O. Mahmoodi, K. Tabatabaeian and A. Fallah Shojaie, J. Chem. Res. 43 (2019) 135-139.
[28] M. Sheykhan, L. Ma’mani, A. Ebrahimi and A. Heydari, J. Mol. Catal. A: Chem. 335 (2011) 253-261.
[29] L. Ma’mani, M. Sheykhan, A. Heydari, M. Faraji and Y. Yamini,Appl. Catal. A. 377 (2010) 64-69.
[30] Mamaghani, M., Shirini, F., Bassereh, E., Nia, R. H., J. Saudi Chem. Soc. 20 (5) (2016) 570-576.
[31] a) N. Lakshmi, P. Thirumurugan, K. M. Noorulla and P. T. Perumal, Bioorg. Med. Chem. Lett. 20 (2010) 5054-5061. b) P. Borah, P. S. Naidu, S. Majumder and P. Bhuyan, J. Mol. Divers., 2014, 18, 759-767.
[32] A. Hallaoui, S. Chehab, B. Malek, O. Zimou, T. Ghailane, S. Boukhris, A. Souizi and R. Ghailane, ChemistrySelect 4 (2019) 3062-3070.
[33] A. Mulik, P. Hegade, S. Mulik and M. Deshmukh, Res. Chem. Intermediat. 45 (2019) 5641-5647.
[34] M. Mashhadinezhad, M. Mamaghani, M. Rassa and F. Shirini, ChemistrySelect 4 (2019) 4920-4932.
[35] W. Ma, A. Gh. Ebadi, M. Shahbazi Sabil, R. Javahershenas and G. Jimenez, RSC Adv. 9 (2019) 12801-12812.
[36] Gh. Mohammadi Ziarani, A. Badiei, M. Azizi and P. Zarabadi, Iran. J. Chem. Chem. Eng. 30 (2) (2011) 59-65.
[37] P. Mukherjee and R. A. Das, J. Org. Chem. 81(13) (2016) 5513-5524.
[38] A. Ovchinnikova and A. N. Andin, Russ. J. Org. Chem. 49 (2013) 1067-1071.
[39] A. Hasaninejad, N. Golzar, M. Beyrati, A. Zare, and M. M. Doroodmand, J. Mol. Catal. A: Chem. 372 (2013) 137-150.
Iranian Journal of Catalysis
Volume 10, Issue 4
Autumn 2020
Pages 267-276

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