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Synthesis of Phthalazine Derivatives through a One-Pot Three-Component Reaction Using a Highly Efficient and Recyclable Magnetic Cobalt Nanocatalyst

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Abstract

1H-Indazolo[2,1-b]phthalazine-1,6,11-trione derivatives have been synthesized through a one-pot three-component condensation of phthalhydrazide, dimedone, and aromatic aldehydes at 80°C under solvent-free conditions in the presence of a novel Co nanoparticle catalyst. The catalyst was prepared by coating Fe3O4 magnetic nanoparticles with tetraethyl orthosilicate, followed by functionalization with 3-chloropropyl(tri­methoxy)silane and 2-amino-1,3,4-thiadiazole-5(4H)-thione and complexation with cobalt(II) acetate. The superparamagnetic catalyst could be readily recovered by applying an external super magnet and used for several times without significant loss of catalytic activity.

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REFERENCES

  1. Mourad, A.K., Makhlouf, A.A., and Soliman, A.Y., J. Chem. Res., 2019, vol. 44, p. 31. https://doi.org/10.1177/1747519819883840

    Article  CAS  Google Scholar 

  2. Zhang, L., Guan, L-P., Sun, X-Y., Wei, C-X., Chai, K-Y., and Quan, Z-S., Chem. Biol. Drug Des., 2009, vol. 73, p. 313. https://doi.org/10.1111/j.1747-0285.2009.00776.x

    Article  CAS  Google Scholar 

  3. Ryu, C.-K., Park, R.-E., Ma, M.-Y., and Nho, J.-H., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 2577. https://doi.org/10.1016/j.bmcl.2007.02.003

    Article  CAS  Google Scholar 

  4. Li, J., Zhao, Y.-F., Yuan, X.-Y., Xu, J.-X., and Gong, P., Molecules, 2006, vol. 11, p. 574. https://doi.org/10.3390/11070574

    Article  CAS  Google Scholar 

  5. Sinkkonen, J., Ovcharenko, V., Zelenin, K., Bezhan, I., Chakchir, B., Al-Assar, F., and Pihlaja, K., Eur. J. Org. Chem., 2002, vol. 2002, no. 13, p. 2046. https://doi.org/10.1002/1099-0690(200207)2002:13<2046::AID-EJOC2046>3.0.CO;2-C

    Article  Google Scholar 

  6. Nomoto, Y., Obase, H., Takai, H., Teranishi, M., Nakamura, J., and Kubo, K., Chem. Pharm. Bull., 1990, vol. 38, p. 2179. https://doi.org/10.1248/cpb.38.2179

    Article  CAS  Google Scholar 

  7. Watanabe, N., Kabasawa, Y., Takase, Y., Matsukura, M., Miyazaki, K., Ishihara, H., Kodama, K., and Adachi, H., J. Med. Chem., 1998, vol. 41, p. 3367. https://doi.org/10.1021/jm970815r

    Article  CAS  Google Scholar 

  8. Ghahremanzadeh, R., Shakibaei, G.I., and Bazgir, A., Synlett, 2008, vol. 2008, p. 1129. https://doi.org/10.1055/s-2008-1072716

    Article  CAS  Google Scholar 

  9. Ghahremanzadeh, R., Ahadi, S., Sayyafi, M., and Bazgir, A., Tetrahedron Lett., 2008, vol. 29, p. 4479. https://doi.org/10.1016/j.tetlet.2008.05.063

    Article  CAS  Google Scholar 

  10. Grasso, S., De Sarro, G., De Sarro, A., Micale, N., Zappalà, M., Puja, G., Baraldi, M., and De Micheli, C., J. Med. Chem., 2000, vol. 43, p. 2851. https://doi.org/10.1021/jm001002x

    Article  CAS  Google Scholar 

  11. Sheradsky, T. and Moshenberg, R., J. Org. Chem., 1986, vol. 51, p. 3123. https://doi.org/10.1021/jo00366a008

    Article  CAS  Google Scholar 

  12. Heine, H.W., Baclawski, L.M., Bonser, S.M., and Wachob, G.D., J. Org. Chem., 1976, vol. 41, p. 3229. https://doi.org/10.1021/jo00882a002

    Article  CAS  Google Scholar 

  13. Ramtohul, Y.K., James, M.N., and Vederas, J.C., J. Org. Chem., 2002, vol. 67, p. 3169. https://doi.org/10.1021/jo0157831

    Article  CAS  Google Scholar 

  14. Liu, L.-P., Lu, J.-M., and Shi, M., Org. Lett., 2007, vol. 9, p. 1303. https://doi.org/10.1021/ol070178r

    Article  CAS  Google Scholar 

  15. CsXmpai, A., Körmendy, K., and Ruff, F., Tetrahedron, 1991, vol. 47, p. 4457. https://doi.org/10.1016/S0040-4020(01)87114-3

    Article  Google Scholar 

  16. Amarasekara, A.S. and Chandrasekara, S., Org. Lett., 2002, vol., 4, p. 773. https://doi.org/10.1021/ol017256+

  17. Hwang, J.Y., Choi, H.-S., and Gong, Y.-D., Tetrahedron Lett., 2005, vol. 46, p. 3107. https://doi.org/10.1016/j.tetlet.2005.02.154

    Article  CAS  Google Scholar 

  18. Quiroga, J., Mejı́a, D., Insuasty, B., Abonı́a, R., Nogueras, M., Sánchez, A., Cobo, J., and Low, J.N., Tetrahedron, 2001, vol. 57, p. 6947. https://doi.org/10.1016/S0040-4020(01)00649-4

    Article  CAS  Google Scholar 

  19. Quiroga, J., Hormaza, A., Insuasty, B., Ortiz, A., Sánchez, A., and Nogueras, M., J. Heterocycl. Chem., 1998, vol. 35, p. 231. https://doi.org/10.1002/jhet.5570350142

    Article  CAS  Google Scholar 

  20. Tu, S., Fang, F., Li, T., Zhu, S., and Zhang, X., J. Heterocycl. Chem., 2005, vol. 42, p. 707. https://doi.org/10.1002/jhet.5570420436

    Article  CAS  Google Scholar 

  21. Quiroga, J., Insuasty, B., Hormaza, A., Saitz, C., and Jullian, C., J. Heterocycl. Chem., 1998, vol. 35, p. 575. https://doi.org/10.1002/jhet.5570350313

    Article  CAS  Google Scholar 

  22. Shaabani, A., Rahmati, A., and Naderi, S., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 5553. https://doi.org/10.1016/j.bmcl.2005.08.101

    Article  CAS  Google Scholar 

  23. Wang, X., Ma, W.W., Wu, L.Q., and Yan, F.L., J. Chin. Chem. Soc., 2010, vol. 57, p. 1341. https://doi.org/10.1002/jccs.201000198

    Article  CAS  Google Scholar 

  24. Shaterian, H.R., Hosseinian, A., and Ghashang, M., Arkivoc, 2009, vol. 2009, no. 2, p. 59. https://doi.org/10.3998/ark.5550190.0010.207

    Article  Google Scholar 

  25. Shekouhy, M. and Hasaninejad, A., Ultrason. Sonochem., 2012, vol. 19, p. 307. https://doi.org/10.1016/j.ultsonch.2011.07.011

    Article  CAS  Google Scholar 

  26. Sarrafioun, F., Jamehbozorgi, S., and Ramezani, M., Russ. J. Org. Chem., 2019, vol. 55, p. 1777. https://doi.org/10.1134/S1070428019110216

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors are grateful to the Islamic Azad University (Faculty of Sciences, Arak Branch, Arak Iran) and Islamic Azad University (Faculty of Sciences, Hamadan Branch, Hamadan, Iran) for the technical support of this study. No funding was received to assist with the preparation of this manuscript.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Arak Branch, Islamic Azad University, 38361-19131, Arak, Iran

    F. Sarrafioun & M. Ramezani

  2. Department of Chemistry, Faculty of Sciences, Hamedan Branch, Islamic Azad University, 65181-15743, Hamedan, Iran

    S. Jamehbozorgi & V. Izadkhah

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  1. F. Sarrafioun
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  2. S. Jamehbozorgi
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  3. M. Ramezani
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  4. V. Izadkhah
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Correspondence to S. Jamehbozorgi.

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Sarrafioun, F., Jamehbozorgi, S., Ramezani, M. et al. Synthesis of Phthalazine Derivatives through a One-Pot Three-Component Reaction Using a Highly Efficient and Recyclable Magnetic Cobalt Nanocatalyst. Russ J Org Chem 58, 1481–1486 (2022). https://doi.org/10.1134/S1070428022100141

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