Chemistry of Heterocyclic Compounds

, Volume 51, Issue 10, pp 899–902 | Cite as

Green and Catalyst-free One-pot Synthesis Of 2,3-dihydroquinazolin-4(1h)-ones in Water

  • Abolfazl OlyaeiEmail author
  • Fatemeh Rahbarian
  • Mahdieh SadeghpourEmail author
A facile and highly efficient protocol was successfully applied to synthesize mono- and disubstituted dihydroquinazolinones through a three-component coupling reaction of isatoic anhydride, aniline or ammonium acetate, and aromatic aldehydes in refluxing water with excellent yield without using any catalysts. The protocol avoids the use of hazardous solvents and chromatographic separation. The generality and functional tolerance of this convergent and environmentally benign method is demonstrated.


aromatic aldehyde dihydroquinazolinone isatoic anhydride 


The authors thank the Research Council of Payame Noor University for financial support.


  1. 1.
    Cox, R. J.; O'Hagan, D. J. Chem. Soc. Perkin, Trans. 1 1991, 1, 2537.Google Scholar
  2. 2.
    Bartroli, J.; Turmo, E.; Alguero, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. J. Med. Chem. 1998, 41, 1869.CrossRefGoogle Scholar
  3. 3.
    El-Sabbagh, O. I.; Ibrahim, S. M.; Baraka, M. M.; Kothayer, H. Arch. Pharm. 2010, 343, 274.Google Scholar
  4. 4.
    Rudolph, J.; Esler, W. P.; O'Connor, S.; Coish, P. D.; Wickens, P. L.; Brands, M.; Bierer, D. E.; Bloomquist, B. T.; Bondar, G.; Chen, L.; Chuang, C.-Y.; Claus, T. H.; Fathi, Z.; Fu, W.; Khire, U. R.; Kristie, J. A.; Liu, X.-G.; Lowe, D. B.; McClure, A. C.; Michels, M.; Ortiz, A. A.; Ramsden, P. D.; Schoenleber, R. W.; Shelekhin, T. E.; Vakalopoulos, A.; Tang, W.; Wang, L.; Yi, L.; Gardell, S. J.; Livingston, J. N.; Sweet, L. J.; Bullock, W. H. J. Med. Chem. 2007, 50, 5202.CrossRefGoogle Scholar
  5. 5.
    Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479.CrossRefGoogle Scholar
  6. 6.
    Alaimo, R. J.; Russell, H. E. J. Med. Chem. 1972, 15, 335.CrossRefGoogle Scholar
  7. 7.
    White, D. C.; Greenwood, T. D.; Downey, A. L.; Bloomquist, J. R.; Wolfe, J. F. Bioorg. Med. Chem. 2004, 12, 5711.CrossRefGoogle Scholar
  8. 8.
    Abdel-Jalil, R. J.; Volter, W.; Saeed, M. Tetrahedron Lett. 2004, 45, 3475.CrossRefGoogle Scholar
  9. 9.
    Lopez, S. E.; Rosales, M. E.; Urdaneta, N.; Godoy, M. V.; Charris, J. E. J. Chem. Res. 2000, 258.Google Scholar
  10. 10.
    Corbett, J. W.; Ko, S. S.; Rodgers, J. D.; Gearhart, L. A.; Magnus, N. A.; Bachheler, L. T.; Diamond, S.; Jeffey, K.; Trainor, S.; Anderson, G. L.; Erickson-Vitanen, P. S. J. Med. Chem. 2000, 43, 2019.CrossRefGoogle Scholar
  11. 11.
    Liu, J. F.; Lee, J.; Dalton, A. M.; Bi, G.; Yu, L.; Baldino, C. M.; McElory, E.; Brown, M. Tetrahedron Lett. 2005, 46, 1241.CrossRefGoogle Scholar
  12. 12.
    Magyar, T.; Miklós, F.; Lázár, L.; Fülöp, F. Chem. Heterocycl. Compd. 2015, 50, 1464. [Khim. Geterotsikl. Soedin. 2014, 1590.]Google Scholar
  13. 13.
    Fozooni, S.; Firoozi, H. Chem. Heterocycl. Compd. 2015, 51, 340. [Khim. Geterotsikl. Soedin. 2015, 51, 340.]Google Scholar
  14. 14.
    Wang, M.; Zhang, T. T.; Gao, J. J.; Liang, Y. Chem. Heterocycl. Compd. 2012, 48, 897. [Khim. Geterotsikl. Soedin. 2012, 965.]Google Scholar
  15. 15.
    Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M. Synth. Commun. 2006, 36, 2287.CrossRefGoogle Scholar
  16. 16.
    Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M. A.; Agheb, M.; Heydari, S. Catal. Commun. 2008, 9, 785.CrossRefGoogle Scholar
  17. 17.
    Wang, L. M.; Hu, L.; Shao, J. H.; Yu, J. J.; Zhang, L. J. Fluorine Chem. 2008, 129, 1139.CrossRefGoogle Scholar
  18. 18.
    Rostamizadeh, S.; Amani, A. M.; Mahdavinia, G. H.; Sepehrian, H.; Ebrahimi, S. Synthesis 2010, 1356.Google Scholar
  19. 19.
    Surpur, M. P.; Singh, P. R.; Patil, S. B.; Samant, S. D. Synth. Commun. 2007, 37, 1965.CrossRefGoogle Scholar
  20. 20.
    Chen, J. X.; Wu, D. Z.; He, F.; Liu, M. C.; Wu, H. Y.; Ding, J. C.; Su, W. K. Tetrahedron Lett. 2008, 49, 3814.CrossRefGoogle Scholar
  21. 21.
    Baghbanzadeh, M.; Salehi, P.; Dabiri, M.; Kozehgary, G. Synthesis 2006, 344.Google Scholar
  22. 22.
    Shaterian, H. R.; Oveisi, A. R.; Honarmand, M. Synth. Commun. 2010, 40, 1231.CrossRefGoogle Scholar
  23. 23.
    Ghashang, M.; Azizi, K.; Moulavi-Pordanjani, H.; Shaterian, H. R. Chin. J. Chem. 2011, 29, 1617.CrossRefGoogle Scholar
  24. 24.
    Yoo, C. L.; Fettinger, J. C.; Kurth, M. J. J. Org. Chem. 2005, 70, 6941.CrossRefGoogle Scholar
  25. 25.
    Baghbanzadeh, M.; Dabiri, M.; Salehi, P. Heterocycles 2008, 75, 2809.CrossRefGoogle Scholar
  26. 26.
    Niknam, K.; Mohammadizadeh, M. R.; Mirzaee, S. Chin. J. Chem. 2011, 29, 1417.CrossRefGoogle Scholar
  27. 27.
    Kassaee, M. Z.; Rostamizadeh, S.; Shadjou, N.; Motamedi, E.; Esmaeelzadeh, M. J. Heterocycl. Chem. 2010, 47, 1421.CrossRefGoogle Scholar
  28. 28.
    Zhang, Z. H.; Lu, H. Y.; Yang, S. H.; Gao, J. W. J. Comb. Chem. 2010, 12, 643.CrossRefGoogle Scholar
  29. 29.
    Safari, J.; Gandomi-Ravandi, S. J. Mol. Struct. 2014, 1072, 173.CrossRefGoogle Scholar
  30. 30.
    Dindulkar, S. D.; Oh, J.; Arole, V. M.; Jeong, Y. T. C. R. Chim. 2014, 17, 971.CrossRefGoogle Scholar
  31. 31.
    Ghashang, M. Orient. J. Chem. 2012, 28, 1213.CrossRefGoogle Scholar
  32. 32.
    Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, G.; Mohammadi, A. A. Tetrahedron Lett. 2005, 46, 6123.CrossRefGoogle Scholar
  33. 33.
    Bharathi, A.; Roopan, S. M.; Kajbafvala, A.; Padmaja, R. D.; Darsana, M. S.; Kumari, G. N. Chin. Chem. Lett. 2014, 25, 324.CrossRefGoogle Scholar
  34. 34.
    Darvatkar, N. B.; Bhilare, S. V.; Deorukhkar, A. R.; Raut, D. G.; Salunkhe, M. M. Green Chem. Lett. Rev. 2010, 3, 301.CrossRefGoogle Scholar
  35. 35.
    Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.CrossRefGoogle Scholar
  36. 36.
    Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.CrossRefGoogle Scholar
  37. 37.
    Kumaravel, K.; Vasuki, G. Curr. Org. Chem. 2009, 13, 1820.CrossRefGoogle Scholar
  38. 38.
    Water in Organic Synthesis; Workbench Edition (Science of Synthesis); Kobayashi, S., Ed.; Thieme: Stuttgart, New York, 2012.Google Scholar
  39. 39.
    Hailes, H. C. Org. Process Res. Dev. 2007, 11, 114.CrossRefGoogle Scholar
  40. 40.
    Olyaei, A.; Gesmati, F.; Sadeghpour, M.; Shams, B.; Alizadeh, M. Synth. Commun. 2012, 42, 1650.CrossRefGoogle Scholar
  41. 41.
    Olyaei, A.; Karbalaei Karimi, M.; Razeghi, R. Tetrahedron Lett. 2013, 54, 5730.CrossRefGoogle Scholar
  42. 42.
    Olyaei, A., Ghodrat Alidoust, M. Synth. Commun. 2015, 45, 94.CrossRefGoogle Scholar
  43. 43.
    Karimi-Jaberi, Z.; Arjmandi, R. Monatsh. Chem. 2011, 142, 631.CrossRefGoogle Scholar
  44. 44.
    Ghorbani-Choghamarani, A.; Taghipour, T. Lett. Org. Chem. 2011, 8, 470.CrossRefGoogle Scholar
  45. 45.
    Santra, S.; Rahman, Anupam Roy, M.; Majee, A.; Hajra, A. Catal. Commun. 2014, 49, 52.Google Scholar
  46. 46.
    Chen, J. X.; Wu, D. Z.; He, F.; Liu, M. C.; Wu, H. Y.; Ding, J. C.; Su, W. K. Tetrahedron Lett. 2008, 49, 3814.CrossRefGoogle Scholar
  47. 47.
    Rostamizadeh, S.; Amani, A. M.; Aryan, R.; Ghaieni, H. R.; Shadjou, N. Synth. Commun. 2008, 38, 3567.CrossRefGoogle Scholar
  48. 48.
    Niknam, K.; Jafarpour, N.; Niknam, E. Chin. Chem. Lett. 2011, 22, 69.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor UniversityTehranIran
  2. 2.Department of Chemistry, College of Science, Takestan BranchIslamic Azad UniversityTakestanIran

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