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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Green Synthesis of Mono, Bis and Tris Aminobenzochromenes and Benzopyranochromenes using Fe3O4@Sio2@ Vanillin/Vitamin B1 Nanoparticles: A New, Mild, Simple and Effective Bronsted Acid Catalyst for the Synthesis of Chromenes

Author(s): Leila Zare Fekri*, Mohaddeseh Kadivar-Kalmarzi and Zahra Hojjati-Zolpirani

Volume 20, Issue 4, 2023

Published on: 28 October, 2022

Page: [470 - 483] Pages: 14

DOI: 10.2174/1570179419666220822141726

Price: $65

Abstract

Objective: Vanillin/Vitamin B1 (Thiamine) supported Fe3O4@Sio2 nanoparticles (Fe3O4 @SP@VT) were synthesized and thoroughly analyzed, and were used for the green and efficient synthesis of chromenes using the multicomponent reaction of aldehyde, malononitrile and 4-hydroxy coumarin, as well as the multicomponent reaction of aldehyde, α-naphthol or β–naphthol and 4-hydroxy coumarin.

Methods: The reaction was performed under grinding conditions, and at the end of the reaction, the catalyst was separated in the presence of a strong magnet and can be recovered 10 times.

Results: The advantages of this method are high purity of products, short times, higher yield, easy separation and cheap raw materials.

Conclusion: We have developed Fe3O4@SP@VT catalyzed multicomponent synthesis of aminobenzochromenes using the reaction of benzaldehyde, malononitrile and naphthol and multicomponent synthesis of benzopyranochromenes using benzaldehyde, 4-hydroxycoumarin and β-naphthol under grind technique.

Keywords: Vanillin/Vitamin B1 (Thiamine) supported Fe3O4@SiO2 nanoparticles, aminobenzochromenes, benzopyranochromenes, Green chemistry

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[1]
Zhang, Zh.; Zheng, Ch.; Yuan, A. One-pot multicomponent synthesis of 2-amino-4-aryl-4H-benzo[h]chromene derivatives. Polycycl. Aromat. Compd., 2020, 40(5), 1397-1405.
[http://dx.doi.org/10.1080/10406638.2018.1553196]
[2]
Okasha, R.M.; Alblewi, F.F.; Afifi, T.H.; Naqvi, A.; Fouda, A.M.; Al-Dies, A.M.; El-Agrody, A.M. Design of new benzo[h]chromene derivatives: Antitumor activities and structure-activity relationships of the 2,3-positions and fused rings at the 2,3-positions. Molecules, 2017, 22(3), 479-497.
[http://dx.doi.org/10.3390/molecules22030479] [PMID: 28335470]
[3]
El-Agrody, A.M.; Al-Dies, A.M.; Fouda, A.M. Microwave assisted synthesis of 2-amino-6-methoxy-4H-benzo[h]chromene derivatives. Eur. J. Chem., 2014, 5(1), 133-137.
[http://dx.doi.org/10.5155/eurjchem.5.1.133-137.923]
[4]
Matloubi Moghaddam, F.; Eslami, M.; Hoda, G. Cysteic acid grafted to magnetic graphene oxide as a promising recoverable solid acid catalyst for the synthesis of diverse 4H-chromene. Sci. Rep., 2020, 10(1), 20968-20982.
[http://dx.doi.org/10.1038/s41598-020-77872-8] [PMID: 33262479]
[5]
Abdolmohammadi, Sh.; Afsharpour, M.; Keshavarz-Fatideh, Sh. An efficient green synthesis of 3-amino-1H-chromenes catalyzed by ZnO nanoparticles Thin-film. S. Afr. J. Chem., 2014, 67, 203-210.
[6]
Sehemi, A.G.; Irfan, A.; El-Agrody, A.M. Synthesis, characterization and DFT study of 4H-benzo[h]chromene derivatives. J. Mol. Struct., 2012, 1018, 171-175.
[http://dx.doi.org/10.1016/j.molstruc.2012.03.018]
[7]
Daqing, Sh.; Shu, Zh.; Qiya, Zh.; Xiangshan, W.; Shujiang, T.; Hongwen, H. Clean synthesis of benzo[h]chromene derivatives in water. Youji Huaxue, 2003, 23, 1419-1421.
[8]
Mohammadipour, B.; Bamoniri, A.; Mirjalili, B.F. Green one-pot three-component synthesis of 4H-chromenes in the presence of nano-aoline/BF3/Fe3O4 as a super paramagnetic nanocatalyst. Sci. Iran., 2020, 27, 1216-1225.
[9]
Behbahani, F.K.; Mehraban, S. Synthesis of 2-amino-3-cyano-7-hydroxy-4H-chromenes using L-proline as a biocatalyst. J. Korea. Chem. Soc, 2015, 59, 284-288.
[10]
Fekri, L.Z.; Nikpassand, M.; Mostaghim, S.; Marvi, O. Green catalyst-free multi-component synthesis of amino benzo chromenes in deep eutectic solvents. Org. Prep. Proced. Int., 2020, 52(2), 81-90.
[http://dx.doi.org/10.1080/00304948.2020.1714319]
[11]
Fekri, L.Z.; Barazandehdoust, M. Microwave-assisted synthesis of aminobenzochromenes using potassium 2-oxoimidazolidine 1,3-diide in water. Polycycl. Aromat. Compd., 2021, 41(6), 1274-1283.
[http://dx.doi.org/10.1080/10406638.2019.1672200]
[12]
Sunderhaus, J.D.; Martin, S.F. Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chemistry, 2009, 15(6), 1300-1308.
[http://dx.doi.org/10.1002/chem.200802140] [PMID: 19132705]
[13]
Graebin, C.S.; Ribeiro, F.V.; Rogério, K.R.; Kümmerle, A.E. Multicomponent reactions for the synthesis of bioactive compounds: A review. Curr. Org. Synth., 2019, 16(6), 855-899.
[http://dx.doi.org/10.2174/1570179416666190718153703] [PMID: 31984910]
[14]
Fekri, L.Z.; Nikpassand, M.; Pourmirzajani, S.; Aghazadeh, B. Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of pyrano[3,2-c]chromen-5(4H)-ones. RSC Adv, 2018, 8(40), 22313-22320.
[http://dx.doi.org/10.1039/C8RA02572J] [PMID: 35539722]
[15]
Zare, L.; Mahmoodi, N.O.; Yahyazadeh, A.; Mamaghani, M.; Tabatabaeian, K. An efficient chemo-and regioselective three-component synthesis of pyridazinones and phthalazinones using activated KSF. Chin. Chem. Lett., 2010, 21(5), 538-541.
[http://dx.doi.org/10.1016/j.cclet.2009.11.032]
[16]
Zhang, Q.; Yang, X.; Guan, J. Applications of magnetic nanomaterials in heterogeneous catalysis. ACS Appl. Nano Mater., 2019, 2(8), 4681-4697.
[http://dx.doi.org/10.1021/acsanm.9b00976]
[17]
Nezami, Z.; Eshghi, H. Nanomagnetic catalysis (Fe3O4@S–TiO2): A novel magnetically nano catalyst for the synthesis of new highly substituted tetrahydropyridine derivatives under solvent-free conditions. J. Iran. Chem. Soc, 2021, 18(8), 1997-2008.
[http://dx.doi.org/10.1007/s13738-021-02170-7]
[18]
Veisi, H.; Ozturk, T.; Karmakar, B.; Tamoradi, T.; Hemmati, S. in situ decorated Pd NPs on chitosan-encapsulated Fe3O4/SiO2-NH2 as magnetic catalyst in suzuki-miyaura coupling and 4-nitrophenol reduction. Carbohydr. Polym., 2020, 235, 115966-115967.
[http://dx.doi.org/10.1016/j.carbpol.2020.115966] [PMID: 32122500]
[19]
Akkok, M.; Bugday, N.; Altin, S.; Kiraz, N.; Yasar, S.; Ozdemir, I. N-heterocyclic carbene Pd(II) complex supported on Fe3O4@SiO2: Highly active, reusable and magnetically separable catalyst for Suzuki-Miyaura cross-coupling reactions in aqueous media. J. Organomet. Chem., 2021, 943, 121823-123841.
[http://dx.doi.org/10.1016/j.jorganchem.2021.121823]
[20]
Nikpassand, M.; Pourkarim, Z. NiFe2O4@SiO2 n Pr@glucose Catalyzed Synthesis of Novel 5-pyrazolin-1,2,4- triazazolidine-3-ones (thiones). Curr. Org. Synth., 2021, 18(1), 91-99.
[http://dx.doi.org/10.2174/1570179417666200924150004] [PMID: 32972345]
[21]
Gao, G.; Di, J-Q.; Zhang, H.Y.; Mo, L.P.; Zhang, Z.H. A magnetic metal organic framework material as a highly efficient and recyclable catalyst for synthesis of cyclohexenone derivatives. J. Catal., 2020, 387, 39-46.
[http://dx.doi.org/10.1016/j.jcat.2020.04.013]
[22]
Zhang, M.; Liu, Y.H.; Shang, Z.R.; Hu, H.Ch.; Zhang, Z.H. Supported molybdenum on graphene oxide/Fe3O4: An efficient, magnetically separable catalyst for one-pot construction of spiro-oxindole dihydropyridines in deep eutectic solvent under microwave irradiation. Catal. Commun., 2017, 88, 39-44.
[http://dx.doi.org/10.1016/j.catcom.2016.09.028]
[23]
Chen, M.N.; Mo, L.P.; Cui, Z.S.; Zhang, Z.H. Magnetic nanocatalysts: Synthesis and application in multicomponent reactions. Curr. Opin. Green Sustain. Chem., 2019, 15, 27-37.
[http://dx.doi.org/10.1016/j.cogsc.2018.08.009]
[24]
Xu, L.; Zhang, S.Z.; Li, W.; Zhang, Z.H. Visible-light-mediated oxidative amidation of aldehydes by using magnetic CdS quantum dots as a photocatalyst. Chemistry, 2021, 27(17), 5483-5491.
[http://dx.doi.org/10.1002/chem.202005138] [PMID: 33403733]
[25]
Karami, B.; Ghashghaee, V.; Khodabakhshi, S. Novel silica tungstic acid (STA): Preparation, characterization and its first catalytic application in synthesis of new benzimidazoles. Catal. Commun., 2012, 20, 71-75.
[http://dx.doi.org/10.1016/j.catcom.2012.01.012]
[26]
Sheykhan, M.; Mohammadquli, M.; Heydari, A. A new and green synthesis of formamidines by γ-Fe2O3@ SiO2-HBF4 nanoparticles as a robust and magnetically recoverable catalyst. J. Mol. Struct., 2012, 1027, 156-161.
[http://dx.doi.org/10.1016/j.molstruc.2012.06.009]
[27]
Patil, A.V.; Bandgar, B.P.; Lee, S-H. Silica supported fluoroboric acid: An efficient and reusable heterogeneous catalyst for facile synthesis of 2-aliphatic benzothiazoles, benzoxazoles, benzimidazoles and imidazo[4,5-b]pyridines. Bull. Korean Chem. Soc., 2010, 31(6), 1719-1722.
[http://dx.doi.org/10.5012/bkcs.2010.31.6.1719]
[28]
Kattimani, P.P.; Kamble, R.R.; Meti, G.Y. Expedient synthesis of benzimidazoles using amides. RSC Advances, 2015, 5(37), 29447-29455.
[http://dx.doi.org/10.1039/C5RA00021A]
[29]
Rasal, K.B.; Yadav, G.D. Carbon dioxide mediated novel synthesis of quinazoline-2,4(1H,3H)-dione in water. Org. Process Res. Dev., 2016, 4(12), 2067-2073.
[http://dx.doi.org/10.1021/acs.oprd.6b00244]
[30]
Zare Fekri, L.; Darya-Laal, A.R. NiFe2O4@ SiO2@ amino glucose magnetic nanoparticle as a green, effective and magnetically separable catalyst for the synthesis of xanthene-ones under solvent-free condition. Polycycl. Aromat. Compd., 2020, 40(5), 1539-1556.
[http://dx.doi.org/10.1080/10406638.2018.1559207]
[31]
Fekri, L.Z.; Zeinali, S. Copper/Schiff‐base complex immobilized on amine functionalized silica mesoporous magnetic nanoparticles under solvent‐free condition: A facile and new avenue for the synthesis of thiazolidin‐4‐ones. Appl. Organomet. Chem., 2020, 34(6), e5629.
[http://dx.doi.org/10.1002/aoc.5629]
[32]
Nikpassand, M.; Fekri, L.Z.; Nabatzadeh, M. Fe3O4@SiO2@KIT-6 as an efficient and reusable catalyst for the synthesis of novel derivatives of 3,3′-((Aryl-1-phenyl-1H-pyrazol-4- yl)methylene)bis (1H-indole). Comb. Chem. High Throughput Screen., 2017, 20(6), 533-538.
[http://dx.doi.org/10.2174/1386207320666170425123248] [PMID: 28443502]
[33]
Fekri, L.Z.; Nikpassand, M. Ultrasound-promoted friedel-crafts acylation of arenes and cyclic anhydrides catalyzed by ionic liquid of [bmim] Br/AlCl3. Russ. J. Gen. Chem., 2014, 84(9), 1825-1829.
[http://dx.doi.org/10.1134/S107036321409031X]
[34]
Zare Fekri, L.; Farjood, M. A new multicomponent reaction for the synthesis of amides. Org. Prep. Proced. Int., 2021, 53(3), 291-300.
[http://dx.doi.org/10.1080/00304948.2021.1880217]
[35]
Torabi, M.; Fekri, L.Z.; Nikpassand, M. Synthesis, characterization and application of Fe3O4@ silicapropyl@ vaniline-covalented isoniazid-copper (I) nanocomposite as a new, mild, effective and magnetically recoverable Lewis acid catalyst for the synthesis of acridines and novel azoacridines. J. Mol. Struct., 2022, 1250, 131761-131774.
[http://dx.doi.org/10.1016/j.molstruc.2021.131761]
[36]
Nikpassand, M.; Zare Fekri, L.; Farokhian, P. Synthesis of novel derivatives of benzoxazole in bis-ionic liquid [BDBDIm]. Br. Synth. Commun., 2015, 45(20), 2303-2310.
[http://dx.doi.org/10.1080/00397911.2015.1077256]

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