Abstract
In this work, the surface of Fe3O4 nanoparticles was functionalized with the glycine, furfural, and cobalt (II) nitrate hexahydrate to synthesize a novel support nanocatalyst (Fe3O4@gly@Furfural@Co(NO3)2). The characteristics of the nanocatalyst were confirmed by various techniques, such as energy-dispersive X-ray spectroscopy (EDX), Fourier transform infrared spectrometer, EDX mapping, scanning electron microscopy, X-ray diffraction, thermal gravimetric/derivative thermal gravimetric, vibrating sample magnetometer, and TEM. Finally, the performance of the nanocatalyst was investigated for the one-pot multicomponent synthesis of benzo[b]pyran and pyrano[2,3-d] pyrimidine derivatives. The good–excellent yield of the products was achieved in a green solvent under mild conditions at short reaction time. In addition, the green heterogeneous catalyst has features, such as environmental friendliness, easy separation from the reaction mixture by an external magnet, high catalytic activity, and reusability up to 6 stages without significant reduction of its catalytic activity.
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References
G.H. Mohammadi Ziarani, Z. Kheilkordi, F. Mohajer, A. Badiei, R. Luque, RSC Adv. 11, 17456 (2021)
H. Faroughi Niya, N. Hazeri, M. Fatahpour, M.T. Maghsoodlou, Res. Chem. Intermed. 46, 3651 (2020)
D. Wang, J. He, N. Rosenzweig, Z. Rosenzweig, Nano Lett. 4, 409 (2004)
A.K. Gupta, M. Gupta, Biomaterials 26, 3995 (2005)
J.M. Perez, T. Ooughin, F.J. Simone, R. Weissleder, L. Josephson, J. Am. Chem. Soc. 124, 2856 (2002)
A. Ito, Y. Kuga, H. Honda, H. Kikkawa, A. Horiuchi, Y. Watanabe, T. Kobayashi, Cancer Lett. 212, 167 (2004)
X.J. Zhu, Sci. Iran. 18, 1627 (2011)
A.K. Gupta, A.S. Curtis, J. Mater. Sci. 15, 493 (2004)
H. Faroughi Niya, N. Hazeri, M. Fatahpour, M.T. Maghsoodlou, Res. Chem. Intermed. 46, 1685 (2019)
M. Mohammadi, M. Khodamoradi, B. Tahmasbi, K. Bahrami, A. Ghorbani-Choghamarani, J. Ind. Eng. Chem. 97, 1 (2021)
M. Kazemi, M. Mohammadi, Appl. Organomet. Chem. 34, e5400 (2019)
F. Ghobakhloo, D. Azarifar, M. Mohammadi, H. Keypour, H. Zeynali, Inorg. Chem. 61, 4786 (2022)
M. Mohammadi, A. Ghorbani-Choghamarandi, Res. Chem. Intermed. 48, 2641 (2022)
A. Ghorbani-Choghamarandi, M. Mohammadi, L. Shiri, Z. Taherinia, Res. Chem. Intermed. 45, 5705 (2019)
S. Motahari, A. Khazaei, Polycycl. Aromat. Compd. 43, 945 (2021)
M. Rezaie Kahkhaie, N. Hazeri, M.T. Maghsoodlou, A. Yazdani-Elah-Abadi, Res. Chem. Intermed. 47, 5007 (2021)
Q. Zhang, W. Cui, H. Guo, B. Wang, H. Wang, J. Zhang, W. Li, J. Exp. NanoSci. 17, 326 (2022)
T. Tamoradi, S.M. Mousavi, M. Mohammadi, Chem. Select. 5, 5077 (2020)
M. Mohammadi, A. Ghorbani-Choghamarani, N. Hussain-Khil, Phys. Chem. Solids. 177, 111300 (2023)
A. Nikseresht, R. Bagherinia, M. Mohammadi, R. Mehrvar, RSC Adv. 13, 674 (2023)
A. Ghorbani-Chghamarandi, M. Mohammadi, T. Tamoradi, M. Ghadermazi, Polyhedron 158, 25 (2019)
R. Achagar, A. Elmakssoudi, A. Thoume, M. Dakir, A. Elamrani, Y. Zouheir, M. Zahouily, Z. Ait-Touchente, J. Jamaleddine, M.M. Chehimi, Appl. Sci. 12, 5487 (2022)
B. Shaabani, H. Maleki, J. Rakhtshah, J. Organomet. Chem. 897, 139 (2019)
M. Maleki, M. Azizi, Z. Emdadi, Green Chem. Lett. Rev. 11, 573 (2018)
B. Adrom, N. Hazeri, M. Lashkari, M.T. Maghsoodlou, J. Chem. Res. 40, 458 (2016)
D. Dharmendra, P. Chundawat, Y. Vyas, P. Chaubisa, M. Kumawat, C. Ameta, Sustain Chem Pharm. 28, (2022)
N. Zheng, Q. Hao, K. Lin, J. Pan, Y. Li, W. Zhou, Bioorgan. Med. Chem. Lett. 29, 225 (2019)
M. Davidson, P. Ma, E.A. Stein, A.M. Guotto Jr., A. Raza, R. Chitra, H. Hutchinson, Am. J. Cardiol. 89, 268 (2002)
J.S. Debenham, C. Madsen-Duggan, M.J. Clements, T.F. Walsh, J.T. Kuethe, M. Reibarkh, S.P. Salowe, L.M. Sonatore, R. Hajdu, J.A. Milligan, J. Med. Chem. 59, 11039 (2016)
L. Sorbera, J. Castaner, Drags Future 30, 765 (2005)
J.A. Makawana, M.P. Patel, R.G. Patel, Arch. Pharm. 345, 314 (2012)
A. Venkatesham, R.S. Rao, K. Nagaiah, J.S. Yadav, G. Roopa Jones, S.J. Basha, B. Sridhar, A. Addlagatta, MedChemComm 3, 652 (2012)
A.R. Saundane, K. Vijaykumar, A.V. Vaijinath, Bioorg. Med. Chem. Lett 23, 1978 (2013)
S.A. Patil, J. Wang, X.S. Li, J.J. Chen, T.S. Jones, A. HosniAhmed, R. Patil, W.L. Seibel, W. Li, D.D. Miller, Bioorg. Med. Chem. Lett. 22, 4458 (2012)
E. Alimohammadi, K. Khosravi, A.M. Zolfigol, J. Iran. Chem. Soc. 19, 4721 (2022)
T.E. Ali, M.A. Assiri, A.A. Shati, M.Y. Alfaifi, S.E.I. Elbehairi, Russ. J. Org. Chem. 58, 106 (2022)
S. Tabassum, K.R. Sunaja Devi, S. Govindaraju, Mater. Today Proc. 45, 3716 (2021)
A. Saha, S. Payra, A. Asatkar, A.R. Patel, S. Banerjee, Curr. Organocatal. 6, 177 (2019)
K.C. Barick, P.A. Hassan, J. Colloid Interface Sci. 369, 96 (2012)
K. Kumar Gangu, S. Maddila, S. Babu Mukkamala, S.B. Jonnalagadda, J. Mol. Struct. 1143, 153 (2017)
S.M. Mousavifar, H. Kefayati, S. Shariati, Appl. Organomet. Chem. 32, e4242 (2018)
K.C. Barick, S. Singh, D. Bahadur, M.A. Lawande, D.P. Patkar, P.A. Hassan, J. Colloid Interface Sci. 418, 120 (2014)
Kh. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Chinese J. Catal. 13, 2245 (2013)
S. Rostamnia, A. Nuri, H. Xin, A. Pourjavadi, S.H. Hosseini, Tetrahedron Lett. 54, 3344 (2013)
F. Mohammadpour, Org. Prep. Proceed. Int. 54, 306 (2022)
N. Azizi, S. Dezfooli, M. Khajeh, M.M. Hashemi, J. Mol. Liq. 186, 76 (2013)
A. Rostami, B. Atashkar, H. Gholami, Catal. Commun. 37, 67 (2013)
D.D. Pham, G. Vo-Thanh, T.N. Le, Synth. Commun 47, 1684 (2017)
B. Maleki, N. Nasiri, R. Tayebee, A. Khojastehnezhad, H.A. Akhlaghi, Rsc Adv. 6, 79128 (2016)
R. Heydari, A. Mansouri, F. Shahrekipour, R. Shahraki, Lett. Org. Chem. 15, 302 (2018)
S. Khaksar, A. Rouhollahpour, S.M. Talesh, J. Fluor. Chem. 141, 11 (2012)
N. Taheri, M. Fallah-Mehrjardi, S. Sayyahi, Bull. Chem. Soc. Ethiop. 32, 531 (2018)
K. Madasamy, S.H. Kumaraguru, V. Sankar, S. Mannathan, M. Kathiresan, New J. Chem. 43, 3795 (2019)
M. Esmaeilpour, J. Javidi, F. Dehghani, F. Nowroozi Dodeji, RSC Adv. 34, 26625 (2015)
A. Pourkazemi, N. Assadi, M. Farahi, A. Zarnegaryan, B. Karami, Acta Chim. Solv. 69, 30 (2022)
H. Alinezhad, M. Tarahomi, B. Maleki, A. Amiri, Appl. Organomet. Chem. 33, e4661 (2019)
M. Bakherad, Gh. Bagherian, A. Rezaeifard, F. Mosavebi, B. Shokoohi, A. Keivanloo, J. Iran. Chem. Soc. 18, 839 (2021)
M. Abaszadeh, S.J. Roudbaraki, M. Ghashang, Org. Prep. Proceed. Int. 51, 255 (2019)
M.A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, Appl. Organomet. Chem. 30, 273 (2016)
S.N. Maddila, S. Maddila, W.E. van Zyl, S.B. Jonnalagadda, Rsc Adv. 5, 37360 (2015)
A.A. Mohammadi, M.R. Asghariganjeh, A. Hadadzahmatkesh, Arab. J. Chem. 10, S2213 (2017)
S. Chauhan, A. Mishra, P. Verma, V. Srivastava, Org. Prep. Proceed. Int. 53, 441 (2021)
A.R. Nesaragi, T. Gasti, T.V. Metra, R.R. Kamble, R.B. Chougale, R.S. Keri, Super Mol. Chem. 7, e202200604 (2022)
D. Azarifar, R. Nejat-Yami, F. Sameri, Z. Akrami, Lett. Org. Chem. 9, 435 (2012)
G. Brahmachari, B. Banerjee, A.C.S. Sustain, Chem. Eng. 2, 2802 (2014)
N. Sheikhan-Shamsabadi, M. Ghashang, Main Group Met. Chem. 40, 19 (2017)
M.M. Heravi, A. Ghods, K. Bakhtiari, F. Derikvand, Synth. Commun. 40, 1927 (2010)
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The authors gratefully appreciate the financial support from the Research Council of University of Sistan and Baluchestan.
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RK (the PhD. student) performed the practical laboratory work and wrote the manuscript. NH (Supervisor, PhD) designed the research project. HFN (Advisor, PhD) helped Miss RK to do her PhD. research project in optimized conditions. MF (Advisor, PhD) helped Miss RK with the formal analysis, writing, and editing of her manuscript.
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Keshani, R., Hazeri, N., Faroughi Niya, H. et al. Synthesis of benzo[b]pyran and pyrano[2,3-d]pyrimidine derivatives using a new superparamagnetic nanocatalyst Fe3O4@gly@Furfural@Co(NO3)2. Res Chem Intermed 49, 3461–3479 (2023). https://doi.org/10.1007/s11164-023-05044-0
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DOI: https://doi.org/10.1007/s11164-023-05044-0