Skip to main content
SpringerLink
Log in

Green Route for the Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-ones Using GO@Fe(ClO4)3 Nanocatalyst under Solvent-Free Conditions

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

An effective and environmentally benign methodology has been proposed for the synthesis of isoxazol-5(4H)-one derivatives using GO@Fe(ClO4)3 nanocatalyst. The one-pot multicomponent reaction of aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate under solvent-free conditions at 100°C afforded the corresponding 4-(arylmethylidene)-3-methyl-1,2-oxazol-5(4H)-ones in good to excellent yields. The developed new protocol is environmentally friendly as it is characterized by safety, atom efficiency, low cost, mild solvent-free conditions, minimal waste, catalyst recyclability, easy workup, and excellent functional group tolerance for the synthesis of structurally diverse isoxazole derivatives. All products were characterized by spectral and analytical methods. Also, some new compounds were synthesized.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme
Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.

Similar content being viewed by others

REFERENCES

  1. Vitaku, E., Smith, D.T., and Njardarson, J.T., J. Med. Chem., 2014, vol. 57, p. 10257. https://doi.org/10.1021/jm501100b

    Article  CAS  PubMed  Google Scholar 

  2. Zhu, J., Mo, J., Lin, H.Z., Chen, Y., and Sun, H.P., Bioorg. Med. Chem., 2018, vol. 26, p. 3065. https://doi.org/10.1016/j.bmc.2018.05.013

    Article  CAS  PubMed  Google Scholar 

  3. Hu, F. and Szostak, M., Adv. Synth. Catal., 2015, vol. 357, p. 2583. https://doi.org/10.1002/adsc.201500319

    Article  CAS  Google Scholar 

  4. De Oliveira Silva, A., McQuade, J., and Szostak, M., Adv. Synth. Catal., 2019, vol. 361, p. 3050. https://doi.org/10.1002/adsc.201900072

    Article  CAS  Google Scholar 

  5. Jadhav, S.Y., Shirame, S.P., Kulkarni, S.D., Patil, S.B., Pasale, S.K., and Bhosale, R.B., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 2575. https://doi.org/10.1016/j.bmcl.2013.02.105

    Article  CAS  PubMed  Google Scholar 

  6. Reddy, K.R., Rao, P.S., Dev, G.J., Poornachandra, Y., Kumar, C.G., Rao, P.S., and Narsaiah, B., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 1661. https://doi.org/10.1016/j.bmcl.2014.02.069

    Article  CAS  Google Scholar 

  7. Breuer, S., Chang, M.W., Yuan, J., and Torbett, B.E., J. Med. Chem., 2012, vol. 55, p. 4968. https://doi.org/10.1021/jm201442t

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Kömürcü, Ş.G., Rollas, S., Yilmaz, N., and Çevıkbaş, A., Drug Metab. Drug Interact., 1995, vol. 12, p. 161. https://doi.org/10.1515/dmdi.1995.12.2.161

    Article  Google Scholar 

  9. Kafle, B., Aher, N.G., Khadka, D., Park, H., and Cho, H., Chem. Asian J., 2011, vol. 6, p. 2073. https://doi.org/10.1002/asia.201100154

    Article  CAS  PubMed  Google Scholar 

  10. Demers, J.P., Hageman, W.E., Johnson, S.G., Klaubert, D.H., Look, R.A., and Moore, J.B., Bioorg. Med. Chem. Lett., 1994, vol. 4, p. 2451. https://doi.org/10.1016/s0960-894x(01)80408-x

    Article  CAS  Google Scholar 

  11. Panathur, N., Gokhale, N., Dalimba, U., Koushik, P.V., Yogeeswari, P., and Sriram, D., Bioorg. Med. Chem. Lett., 2015, vol. 25, p. 2768. https://doi.org/10.1016/j.bmcl.2015.05.015

    Article  CAS  PubMed  Google Scholar 

  12. Zhang, Y.-Q., Ma, J.-J., Wang, C., Li, J.-C., Zhang, D.-N., Zang, X.-H., and Li, J., Chin. J. Org. Chem., 2008, vol. 28, p. 141.

    Google Scholar 

  13. Vekariya, R.H.; Prajapati, N.P., Patel, K.D., Mayur, K., Vekariya, M.K., Dhaval, B., Patel, D.B., Hitesh, D., and Patel, H.D., World J. Pharm. Pharm. Sci., 2017, vol. 6, p. 2003. https://doi.org/10.20959/wjpps201704-9010

    Article  CAS  Google Scholar 

  14. Liu, Q. and Wu, R.-T., J. Chem. Res., Synop., 2011, vol. 35, p. 598. https://doi.org/10.3184/174751911X13176501108975

    Article  CAS  Google Scholar 

  15. Kiyani, H. and Ghorbani, F., Res. Chem. Intermed., 2015, vol. 41, p. 2653. https://doi.org/10.1007/s11164-013-1411-x

    Article  CAS  Google Scholar 

  16. Setamdideh, D., J. Mex. Chem. Soc., 2015, vol. 59, p. 191. https://doi.org/10.29356/jmcs.v59i3.34

    Article  CAS  Google Scholar 

  17. Liu, Q. and Zhang, Y.N., Bull. Korean Chem. Soc., 2011, vol. 32, p. 3559. https://doi.org/10.5012/bkcs.2011.32.10.3559

    Article  CAS  Google Scholar 

  18. Khodja, I.A., Boulcina, R., Boumoud, T., Boumoud, B., and Debache, A., Pharma Chem., 2016, vol. 8, p. 97.

    CAS  Google Scholar 

  19. Pawar, G.T., Gadecar, S.P., Arbad, B.R., and Lande, M.K., Bull. Chem. React. Eng. Cat., 2017, vol. 12, p. 32. https://doi.org/10.9767/bcrec.12.1.655.32-40

    Article  CAS  Google Scholar 

  20. Ghosh, S., Saikh, F., Das, J., and Pramanik, A.K., Tetrahedron Lett., 2013, vol. 54, p. 58. https://doi.org/10.1016/j.tetlet.2012.10.079

    Article  CAS  Google Scholar 

  21. Safari, J., Ahmadzadeh, M., and Zarnegar, Z., Catal. Commun., 2016, vol. 86, p. 91. https://doi.org/10.1016/j.catcom.2016.08.018

    Article  CAS  Google Scholar 

  22. Fozooni, S., Hosseinzadeh, N.G., Hamidian, H., and Akhgar, M.R., J. Braz. Chem. Soc., 2013, vol. 24, p.1649. https://doi.org/10.5935/0103-5053.20130211

    Article  CAS  Google Scholar 

  23. Khandebharad, A.U., Sarda, S.R., Gill, C.H., and Agrawal, B.R., Res. J. Chem. Sci., 2015, vol. 5, p. 27.

    CAS  Google Scholar 

  24. Kiyani, H. and Ghorbani, F., Open J. Org. Chem., 2013, vol. 1, p. 5.

    Google Scholar 

  25. Kiyani, H., Org. Chem.: Indian J., 2013, vol. 9, p. 97.

    CAS  Google Scholar 

  26. Rikani, A.B. and Setamdideh, D., Orient. J. Chem., 2016, vol. 32, p. 1433. https://doi.org/10.13005/ojc/320317

    Article  CAS  Google Scholar 

  27. Kiyani, H. and Ghorbani, F., Heterocycl. Lett., 2013, vol. 3, p. 359.

    CAS  Google Scholar 

  28. Behbahani, F.K. and Ziaei, P., 2012, Chin. J. Chem., vol. 30, p. 65. https://doi.org/10.1002/cjoc.201180461

  29. Behbahani, F.K. and Yektanezhad, T., Monatsh. Chem., 2012, vol. 143, p. 1529. https://doi.org/10.1007/s00706-012-0724-6

    Article  CAS  Google Scholar 

  30. Moniri, Z. and Behbahani, F.K., Scholars Int. J. Chem. Mater. Sci., 2019, vol. 2, p. 115. https://doi.org/10.36348/sijcms.2019.v02i07.002

    Article  Google Scholar 

  31. Irannejad-Gheshlaghchaei, N., Zare, A., Sajadi­khah, S.S., and Banaei, A., Res. Chem. Intermed., 2018, vol. 44, p. 6253. https://doi.org/10.1007/s11164-018-3488-8

    Article  CAS  Google Scholar 

  32. Patil, M.S., Mudaliar, C., and Chaturbhuj, G.U., Tetrahedron Lett., 2017, vol. 58, p. 3256. https://doi.org/10.1016/j.tetlet.2017.07.019

    Article  CAS  Google Scholar 

  33. Pourmousavi, S.A., Fattahi, H.R., Ghorbani, F., Kanaani, A., and Ajloo, D., J. Iran. Chem. Soc., 2018, vol. 15, p. 455. https://doi.org/10.1007/s13738-017-1246-2

    Article  CAS  Google Scholar 

  34. Ahmadzadeh, M., Zarnegar, Z., and Safari, J., Green Chem. Lett. Rev., 2018, vol. 11, p. 78. https://doi.org/10.1080/17518253.2018.1434564

    Article  CAS  Google Scholar 

  35. Saikh, F., Das, J., and Ghosh, S., Tetrahedron Lett., 2013, vol. 54, p. 4679. https://doi.org/10.1016/j.tetlet.2013.06.086

    Article  CAS  Google Scholar 

  36. Khandebharad Amol, U., Sarda Swapnil, R., Gill Charansingh, H., and Agrawal Brijmohan, R., Res. J. Chem. Sci., 2015, vol. 5, p. 1.

    Google Scholar 

  37. Laroum, R. and Debache, A., Synth. Commun., 2018, vol. 48, p. 1876. https://doi.org/10.1080/00397911.2018.1473440

    Article  CAS  Google Scholar 

  38. Wang, Y., Sang, R., Zheng, Y., Guo, L., Guan, M., and Wu, Y., Catal. Commun., 2017, vol. 89, p. 138. https://doi.org/10.1016/j.catcom.2016.09.027

    Article  CAS  Google Scholar 

  39. Heravi, M.M. and Behbahani, F.K., J. Iran. Chem. Soc., 2007, vol. 4, p. 375. https://doi.org/10.1007/bf03247223

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Karaj Branch, Islamic Azad University, 31485-313, Karaj, Iran

    E. Madandar & F. K. Behbahani

Authors
  1. E. Madandar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. F. K. Behbahani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to F. K. Behbahani.

Ethics declarations

The authors declare the absence of conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Madandar, E., Behbahani, F.K. Green Route for the Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-ones Using GO@Fe(ClO4)3 Nanocatalyst under Solvent-Free Conditions. Russ J Org Chem 58, 830–836 (2022). https://doi.org/10.1134/S1070428022060112

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022060112

Keywords:

Search

Navigation