Efficient and greener method synthesis of pyrano [2, 3-c] pyrazole derivatives catalyzed by Fe3O4@L-Cys-SH as reusable catalyst
- Rani Channamma University, Belagavi, P-B, NH-4-591156, Karnataka. India
- Department of Chemistry, Rani Channamma University, Belagavi, P-B, NH-4-591156, Karnataka, India
Received: 2025-03-04
Revised: 2025-05-16
Accepted: 2025-06-06
Published in Issue 2025-09-30
Published Online: 2025-07-01
Copyright (c) 2025 Raju Shekhanavar, Santosh Y. Khatavi, Kantharaju Kamanna (Author)

This work is licensed under a Creative Commons Attribution 4.0 International License.
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Abstract
The present work describes the eco-friendly preparation of magnetic nanoparticles Fe3O4 (MNPs), and further functionalized with L-Cysteine amino acid. Various analytical and spectroscopic techniques used for the characterization of prepared MNPs and its functionalized materials. Further demonstrated utility of this functionalized MNPs for four component one-pot synthesis of pyrano [2, 3-c]pyrazole derivatives. The synthetic approach outlined is rapid, eco-friendly, and allows for the simple isolation of the product. After recrystallization of the crude product gave a chromatographically pure product, this method found an inexpensive and recyclable catalyst, which was achieved up to four cycles for the synthesis of bioactive heterocycles. The synthesized derivatives were characterized using FT-IR, 1H- & 13C-NMR, and LC-MS. Additionally, some of the selected derivatives showed moderate antioxidant activity (5a, five h, 5i, 5j, 5k, 5n, 5p, and 5q) against a reference.
Keywords
- Antioxidant,
- Eco-friendly,
- Functionalized,
- Pyrano [2,3-c] pyrazole,
- Recyclable
References
- D. Y. Lee, H. Li, H. J. Lim, H. J. Lee, R. Jeon, and J. H. Ryu. J. Med. Food, 15 (2012):992-999. DOI: https://doi.org/10.1089/jmf.2012.2275.
- H. Lim, K. Kubota, A. Kobayashi, T. Seki, and T. Ariga. Biosci.Biotech.Biochem., 63 (1999):298 301. DOI:https://doi.org/10.1271/bbb.63.298.
- E. Mukwevho, Z. Ferreira, and A. Ayeleso. Molecules, 19 (2014):19376-19389. DOI: https://doi.org/10.3390/molecules191219376.
- M.S. Subramanian, M.S.G. Nandagopal, S. Amin Nordin, K. Thilakavathy, N.Joseph. Molecules, 25 (2020):4111. DOI:https://doi.org/10.3390/molecules25184111.
- I. Fernandez, N. Khiar. Chem. Rev.,103 (2003): 3651–3706. DOI:https://doi.org/10.1021/cr990372u.
- K. Khosravi, S. Naserifar, and A. Asgari. Lett. Org. Chem., 13(2016):749–756. DOI: https://doi.org/10.2174/1570178614666161123115100.
- A. Padwa, W. H. Bullock, A. D. Dys zlewski. J. Org. Chem., 55(1990):955-964. DOI:https://doi.org/10.1021/jo00290a029.
- R. V. Kupwade. J.Chem.Rev.,1(2019):99-113. DOI: https://doi.org/10.33945/SAMI/JCR.2019.1.99113.
- A. Taketoshi, P. Concepcion, H. Garcia, A. Corma, M. Haruta. Bull. Chem. Soc. Jap., 86 (2013):1412 1418. DOI:https://doi.org/10.1246/bcsj.20130075.
- M. A. Zolfigol, A. Khazaei, M. Safaiee, M .Mokhlesi, R. Rostamian, M. Bagheri, M. Shiri, H. G. Kruger. J. Mole .Catal. A Chem., 370 (2013):80-86. DOI: https://doi.org/10.1016/j.molcata.2012.12.015.
- A. Rostami, J. Akradi. Tetrahedron Lett., 51 (2010):3501-3503. DOI: https://doi.org/10.1016/j.tetlet.2010.04.103.
- A. Bravo, B. Dordi, F. Fontana, F. Minisci. J. Org. Chem., 66 (2001):3232-3234. DOI: https://doi.org/10.1021/jo0017178.
- M. G. Kermanshahi, K. Bahrami. RSC Adv., 9 (2019):36103-36112. DOI: https://doi.org/10.1039/C9RA06221A.
- B. Maleki, S. Hemmati, A. Sedrpoushan, S. S. Ashrafi, H.Veisi. RSC. Adv, 4 (2014):40505-40510. DOI: https://doi.org/10.1039/C4RA06132B.
- H. Golchoubian, F. Hosse. in poor. Molecules, 12 (2007):304-311. DOI: https://doi.org/10.3390/12030304.
- M. S. Mashhoori, R. Sandaroos, A. Z. Moghaddam. Polycycl. Arom.Compd., 42(2022):5067-5085.DOI: https://doi.org/10.1080/10406638.2021.1922470.
- R. Sandaroos, B. Maleki, S. Naderi, S. Peiman. Inorg.Chem.Commun.,
- S. M. Khatami, M. Khalaj, M. Ghashang. Iran. J. Catal., 13 (2023):475–485. DOI: https://doi.org/10.30495/ijc.2023.1993331.2039.
- M. Dehbashi, M. Aliahmad, M.R.M. Shafiee, and M. Ghashang. Phosphorus, Sulfur Relat. Elem., 188 (2013):864-872. DOI: https://doi.org/10.1080/10426507.2012.717139.
- B. Karimi, M. Ghoreishi-Nezhad, and J.H. Clark. Org. Lett., 7 (2005):625–628. DOI: https://doi.org/10.1021/ol047635d.
- C. Raj Kumar, B. Thirumalraj, S. M. Chen, P. Veerakumar, S.-B. Liu. ACS Appl. Mater. Interfaces, 9 (2017):31794–31805. DOI: https://doi.org/10.1021/acsami.7b07645.
- B. Karimi M. Khorasani. ACS Catal, 3 (2013):1657-1664. DOI:https://doi.org/10.1021/cs4003029.
- M. Dabiri, H. E. Tavil, N. F. Lehi, S. K. Movahed, A. M. Salmasi, S. Souri. J.Phys.Chem.Solids,162 (2022):110497. DOI:https://doi.org/10.1016/j.jpcs.2021.110497.
- F. Rajabi, E.Vessally, R. Luque, L.Voskressen sky. Mol. Catal, 515 (2021):111931. DOI: https://doi.org/10.1016/j.mcat.2021.111931.
- M. Jin, J. Wang, B. Wang, Z. Guo, Z. Lv. Micropor. Mesopor. Mat., 277 (2019):84–94. DOI: https://doi.org/10.1016/j.micromeso.2018.10.021.
- A. Sedrpoushan, F. Hosseini-Eshbala, F. Mohanazadeh, and M. Heydari. Appl. Organomet. Chem., 32 (2018):e4004. DOI: https://doi.org/10.1002/aoc.4004.
- S. H. Hosseini, M. Tavakolizadeh, N. Zohreh, R. Soleyman. Organomet.Chem., 32 (2018):e3953. DOI:https://doi.org/10.1002/aoc.3953.
- N. Zohreh, S. H. Hosseini, A. Pourjavadi, R. Soleyman, C. Bennett. J.Indust.Eng.Chem.,44 (2016):73-81. DOI:https://doi.org/10.1016/j.jiec.2016.08.011.
- C. M. Tressler, P. Stonehouse, K. S. Kyler. Green Chem., 18 (2016):4875–4878. DOI: https://doi.org/10.1039/C6GC00725B.
- S. Iraqui, S. S. Kashyap, M. H. Rashid. Nanoscal. Adv., 2 (2020):5790-5802. DOI: https://doi.org/10.1039/D0NA00591F.
- L. Sun, R. Zhang, Z. Wang, L. Ju, E. Cao, and Y. Zhang. J. Mag. Mag. Mater., 421 (2017):65–70. DOI:https://doi.org/10.1016/j.jmmm.2016.08.003.
- R. Hajiarab, M. R. M. Shafiee, M. Ghashang. Polycycl. Aromat. Compd., 43 (2023):2032–2043. DOI: https://doi.org/10.1080/10406638.2022.2039231
- R. Hajiarab, M. R. M. Shafiee, and M. Ghashang. Org. Prep. Proced. Int., 54 (2022):259-267. DOI:https://doi.org/10.1080/00304948.2022.2033064.
- F. Aminsharei, A. Lahijanian, A. Shiehbeigi, S. S. Beiki, and M. Ghashang. Int. J. Biolog. Macromol., 276 (2024):134004. https://doi.org/10.1016/j.ijbiomac.2024.134004.
- F. Rezaei, H. Alinezhad, B. Maleki. Sci Rep, 13 (2023):20562. DOI: https://doi.org/10.1038/s41598 023-47794-2.
- H. Boroum, H. Alinezhad, B. Maleki, and S. Peiman. Polycyclic Compounds, 43 (2023):7853-7869. Aromatic DOI: https://doi.org/10.1080/10406638.2022.2140683.
- R. S. Varma K. P. Naicker. Org. Lett., 1(1999): 189-191. DOI: https://doi.org/10.1021/ol990522n.
- Q. Wang, W. Ma, Q. Tong, G. Du, J. Wang, M. Zhang, H. Jiang, H. Yang, Y. Liu, and M. Cheng. Sci. Rep., 7(2017):7209. DOI: https://doi.org/10.1038/s41598 017-07590-1.
- A. Bayat, M. S. Fard, N. Ehyaei, and M. Mahmoodi Hashemi. RSC Adv., 4(2014):44274 44281. DOI: https://doi.org/10.1039/C4RA07356H.
- Z. Yekke-Ghasemi, M. M. Heravi, M. Malmir, and M. Mirzaei. Sci. Rep., 13 (2023):16752. DOI: https://doi.org/10.1038/s41598-023-43985-z.
- I. A. Al-Masoudi, Y. A. Al-Soud, N. J. Al Salihi, and N. A. Al-Masoudi. Chem. Het erocycl. Compd., 42(2006):1377–1403. https://doi.org/10.1007/s10593-006-0255-3.
- M. M. Pearson, D. Rogers, J. D. Cleary, and S. W. Chapman. Ann Pharmacotherapy, 37 (2003):420–432. DOI: https://doi.org/10.1345/aph.1C261.
- N. D. Greer. Cent., Bayl. 20(2007):188-196. Uni. Med. DOI: https://doi.org/10.1080/08998280.2007.11928283.
- I. A. Guralskiy, V. A. Reshetnikov, I. V. Omelchenko, A. Szebesczyk, E. G. Konteckac, and I. O. Fritskya. J. Mol. Struct., 1127(2017):164–168. DOI: https://doi.org/10.1016/j.molstruc.2016.07.094.
- Y. L. Fan, X. Ke, and M. Liub. J. Heterocycle. Chem., 55(2018):791–802. DOI: https://doi.org/10.1002/jhet.3112.
- M. Onozato, A. Nishigaki, K. Okoshi. Poly. Arom. Comp., 40 ( 2018): 1291-1301. https://doi.org/10.1080/10406638.2018.1540998
- L. Z. Fekri, S. Zeinali. Appl. Organomet. Chem., 17 (2020): 20-40 https://doi.org/10.1002/aoc.5629
- L. Z. Fekr, K. H. Pour, S. Zeinali. J. Organo. chem., 915 (2020):121232-121245. https://doi.org/10.1016/j.jorganchem.2020.121232
- M. N. passand, L. Z. Fekri, R. S. Varma, L. Hassanzadi, F. S. Pashaki. RSC Adv. 12 (2022): 834-844. https://doi.org/10.1039/D1RA08001F
- A. Bhardwaj. O.P. P. I., 57 (2024):189-217. doi: 10.1080/00304948.2024.2431378
- F. S. Ghahfarokhi, A. Ghaemi, M. R. Kakhki. Inorg. Nano-Metal. Chem., 54 (2023):1179-1186. https://doi.org/10.1080/24701556.2023.2166072
- N. Suleymanoglu, R. Ustabas, S. Di, Y. B. Alpasland, Y. Unvere. J. Mol. Struct., 1150(2017):82–87. DOI: https://doi.org/10.1016/j.molstruc.2017.08.075.
- R. Kharb, P. C. Sharma, M. S. Yar. J. En zyme. Inhib. Med. Chem., 26 (2017):1-21. DOI: https://doi.org/10.3109/14756360903524304.
- K. B. Badiger, Giddaerappa, R. Hanumanthappa, L. K. Sannegowda, K. Kamanna. Chem. Select., March 9 (2022) e202104033. https://doi.org/10.1002/slct.202104033
- B. M. Chougala, S. Samundeeswari, M. Holiyachi, L. A. Shastri, S. Dodamani, S. Jalalpure, S. R. Dixit, S. D. Joshi, and V. A. Sunagar. Eur. J. Med. Chem., 125(2017):101–116. DOI: https://doi.org/10.1016/j.ejmech.2016.09.021.
- N. Fu, S. Wang, Y. Zhang, C. Zhang, D. Yang, L. Weng, B. Zhao, and L. Wang. Eur. J. Med. Chem., 136(2017):596–602. DOI: https://doi.org/10.1016/j.ejmech.2017.05.001.
- K. M. Banu, A. Dinakar, C. A. narayanan. Indian J. Pharm. Sci., 61 (1999): 202–205. URL https://www.ijpsonline.com/articles.
- L. Z. Chen, W. W. Sun, L. Bo, J. Q. Wang, C. Xiu, W. J. Tang, J. B. Shi, H. P. Zhou, and X. H. Liu. Eur. J. Med. Chem., 138 (2017):170–181. DOI: https://doi.org/10.1016/j.ejmech.2017.06.044.
- J. Akhtar, A. A. Khan, Z. Ali, R. Haider, M. S. Yar. Eur. J. Med. Chem., 125 (2017):143–189. DOI: https://doi.org/10.1016/j.ejmech.2016.09.023.
- R. Gujjar, A. Marwaha, J. White, L. White, S. Creason, D. M. Shackle ford, J. Baldwin, W. N. Charman, S. Buckner, F. S. Charman, P. K. Rathod, and M. A. Phillips. J. Med. Chem., 52(2009):1864-1872. DOI: https://doi.org/10.1021/jm801343r.
- Y. Q. Hu, C. Gao, S. Zhang, L. Xu, Z. Xu, L. S. Feng, X. Wu, and F. Zhao. Eur. J. Med. Chem., 139 (2017):22-47. https://doi.org/10.1016/j.ejmech.2017.07.061.
- A. Duran, H. N. Dogan, and H. Rol las. Farmaco, 57(2002):559-564. DOI: https://doi.org/10.1016/S0014-827X(02)01248 X.
- X. Wen, Y. Zhou, J. Zeng, and X. Liu. Curr. Topics. Med. Chem., 20(2020):1441–1460. https://doi.org/10.2174/1568026620666200128143230.
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