An Efficient Synthesis of Some Novel Benzo Coumarin Derivatives Under Solvent Conditions from 2-acetyl-benzo[f]chromen-3-one

Year : 2024 | Volume : 02 | Issue : 02 | Page : 33 46
    By

    Mohamad F Ali,

  • Hussniya A. AlDifar,

  • Basma S. Baaiu,

  1. Associate Professor, Department of Chemistry, Faculty of Science, Benghazi University, Benghazi, Libya
  2. Associate Professor, Department of Chemistry, Faculty of Science, Benghazi University, Benghazi, Libya
  3. Associate Professor, Department of Chemistry, Faculty of Science, Benghazi University, Benghazi, Libya

Abstract

The synthesis of the target compounds began with the preparation of 2-[3-dimethylamino[acryloyl-3H-benzo[f]chromen-3-one. This intermediate was obtained through the reaction of 2-acetylbenzo[f]coumarin-3-one with N,N-dimethylformamide dimethyl acetal [DMFDMA[ under reflux conditions in xylene. The enaminone thus formed was subsequently reacted with 6-aminothiouracil in acetic acid, leading to the formation of 2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one. This compound served as a pivotal intermediate for the synthesis of a series of pyridotriazolopyrimidinones. These derivatives were synthesized by reacting compound 6 with various hydrazonoyl halides in the presence of triethylamine and dioxane as a solvent. The structures of all the newly synthesized compounds were confirmed through comprehensive spectroscopic techniques, including nuclear magnetic resonance [NMR], infrared [IR] spectroscopy, and mass spectrometry [MS], as well as elemental analysis. There was also discussion and rationalization of the mechanistic elements of the reactions that produced the end products.

Keywords: 2-hydroxynaphthaldehyde; enaminone; hydrazonoyl halides; pyridotriazolopyrimidinones

[This article belongs to International Journal of Cheminformatics ]

How to cite this article:
Mohamad F Ali, Hussniya A. AlDifar, Basma S. Baaiu. An Efficient Synthesis of Some Novel Benzo Coumarin Derivatives Under Solvent Conditions from 2-acetyl-benzo[f]chromen-3-one. International Journal of Cheminformatics. 2025; 02(02):33-46.
How to cite this URL:
Mohamad F Ali, Hussniya A. AlDifar, Basma S. Baaiu. An Efficient Synthesis of Some Novel Benzo Coumarin Derivatives Under Solvent Conditions from 2-acetyl-benzo[f]chromen-3-one. International Journal of Cheminformatics. 2025; 02(02):33-46. Available from: https://journals.stmjournals.com/ijci/article=2025/view=202213


References

  1. Molnar, M.; Loncˇaric´, M.; Kovacˇ, M. Green chemistry approaches to the synthesis of coumarin derivatives. Curr. Org. Chem. 2020, 24, 4.
  2. Abdel-Aziem, A.; Baaiu, B. S.; Elbazzar, A. W.; Elabbar F. A facile synthesis of some novel thiazoles, arylazothiazoles, and pyrazole linked to thiazolyl coumarin as antibacterial agents. Synth. Commu. 2020, 50(16), 2522.
  3. Abdel-Aziem, A.; Baaiu, B. S.; El-Sawy E. R . Arom. Comp. DOI: 10.1080/10406638.2021.1916543.
  4. Abdel-Aziem, A. J. Heterocycl. 2015, 52, 251.
  5. Mishra, S.; Pandey, A.; Manvati, S. Heliyon. 2020, 6, e03217.
  6. Yerer, M. B.; Dayan, S.; Han, M. I.; Sharma, A.; Tuli, H. S.; Sak, K. Anticancer Agents Med. Chem. 2020, 20(15), 1797.
  7. Xu, Z.; Chen, Q.; Zhang, Y.; Liang, C. Coumarin-based derivatives with potential anti-HIV activity. Fitoterapia. 2021, 150, 104863.
  8. N. Sudha, V. G. sastry, Int. J. Adv. Res, 4 (3) (2016) 1225-1232.
  9. Abdelmohsen, U. R.; Albohy, A.; Abdulrazik, B. S.; Bayoumi, S. A. L.; Malak, L. G.; Khallaf, I. S. A.; Bringmann, G.; Farag, S. F. Natural coumarins as potential anti-SARS-CoV-2agents supported by docking analysis. RSCAdv. 2021,11,16970.
  10. Basappa, V. C.; Penubolu, S.; Achutha, D. K.; Kariyappa, A. K. J. Chem. Sci. 2021, 133, 55.
  11. Sairam, K. V.; Gurupadayya, B. M.; Vishwanathan, B. I.; Chandana, R. S.; Nagesha, D. K. RSC Adv. 2016, 6, 98816.
  12. Abdul Rahman, F. S.; K.Yusufzai, S.; Osman, H.; Mohamad D. J. Phys. Sci. 2016, 27(1), 77.
  13. Schlienger, R.; Kurmann, M.; Drewe, J.; Müller-Spahn, F.; Seifritz, E. Eur Neuropsychpharmacolo. 10(3) (2000) 219–221.
  14. Lengyel, M. SPORTIF-III Altanulmány Vizsgálói, Orv Hetil. 2004,145 (52), 2619.
  15. Williamson, R. C. N.; Lyndon, P.T.; Tudway, A.J.C. Br. J. Cancer.1980, 42 85.
  16. T. Sugino and K. Tanaka, Chem. Lett., 2001, 2, 110.
  17. Moustaha, C.; Abdel-Riheem, N. A.; Abdelamid, A. O. Synth. Commun. 2005, 35, 249.
  18. Anhar Abdel-Aziem a, Huda Refaat Mahmoud Rashdan b, Entesar Mohamed Ahmed Green Chemistry Letters And Reviews 2019, Vol. 12, No. 1, 9–18
  19. Stefanachi A., Leonetti F., Pisani L., Catto M., Carotti A., Molecules, 2018, 23:250
  20. Mohammed E.T., Mustafa Y.F.,  Rev. Pharm, 2020, 11:64
  21. Mustafa Y.F., Kasim S.M., Al-Dabbagh B.M., Al-Shakarchi W.,  Nanosci. [Switzerland[, 2021.
  22. Mustafa Y.F., Khalil R.R., Mohammed E.T.,  Rev. Pharm., 2020, 11:382
  23. Mustafa Y.F., Oglah M.K., Bashir M.K.,  Rev. Pharm., 2020, 11:482
  24. Jung Y., Jung J., Huh Y., Kim D.,  Anal. Methods Chem.,2018
  25. Mustafa Y.F., Mohammed E.T., Khalil R.R.,  J. Chem., 2021, 64:4461
  26. Khalil R.R., Mustafa Y.F.,  Rev. Pharm.,2020, 11:57
  27. Oglah M.K., Bashir M.K., Mustafa Y.F., Mohammed E.T., Khalil R.R.,  Rev. Pharm., 2020, 11:717
  28. Mustafa Y.F., Mohammed E.T., Khalil R.R.,  Rev. Pharm., 2020, 11:570
  29. Oglah M.K., Mustafa Y.F.,  Glob. Pharma Technol., 2020, 12:854
  30. Mustafa Y.F., Abdulaziza N.T., Jasim M.H.,  J. Chem., 2021, 64:1807
  31. Mustafa Y.F., Mohammed N.A.,  Cell. Arch., 2021, 21:1991
  32. Mustafa Y.F., Khalil R.R., Mohammed E.T.,  J. Chem., 2021, 64:3711
  33. Bashir M.K., Mustafa Y.F., Oglah M.K.,  Tche Quim., 2020, 17:871
  34. Mustafa Y.F., Abdulaziz N.T., NeuroQuantology,2021, 19:175
  35. Bashir M.K., Mustafa Y.F., Oglah M.K.,  Rev. Pharm., 2020, 11:175
  36. Mustafa Y.F., Abdulaziz N.T.,  Rev. Pharm., 2020, 11:438
  37. Mahmood A.A.J., Mustafa Y.F., Abdulstaar M.,  Med. J. Malaysia, 2014, 13:3
  38. Aldewachi H., Mustafa Y.F., Najm R., Ammar F.,  Rev. Pharm., 2020, 11:289
  39. Mustafa Y.F.,  Med. Chem. Sci., 2021, 4:612
  40. Salem M.A., Helal M.H., Gouda M.A., Ammar Y.A., El-Gaby M.S.A., Abbas S.Y.,  Commun., 2018, 48:53
Regular Issue Subscription Original Research
Volume 02
Issue 02
Received 29/10/2024
Accepted 07/01/2025
Published 28/02/2025
Publication Time 122 Days
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