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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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References

  1. Cox, R. J.; O'Hagan, D. J. Chem. Soc. Perkin, Trans. 1 1991, 1, 2537.

  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.

    Article  CAS  Google Scholar 

  3. El-Sabbagh, O. I.; Ibrahim, S. M.; Baraka, M. M.; Kothayer, H. Arch. Pharm. 2010, 343, 274.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  6. Alaimo, R. J.; Russell, H. E. J. Med. Chem. 1972, 15, 335.

    Article  CAS  Google Scholar 

  7. White, D. C.; Greenwood, T. D.; Downey, A. L.; Bloomquist, J. R.; Wolfe, J. F. Bioorg. Med. Chem. 2004, 12, 5711.

    Article  CAS  Google Scholar 

  8. Abdel-Jalil, R. J.; Volter, W.; Saeed, M. Tetrahedron Lett. 2004, 45, 3475.

    Article  CAS  Google Scholar 

  9. Lopez, S. E.; Rosales, M. E.; Urdaneta, N.; Godoy, M. V.; Charris, J. E. J. Chem. Res. 2000, 258.

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  12. Magyar, T.; Miklós, F.; Lázár, L.; Fülöp, F. Chem. Heterocycl. Compd. 2015, 50, 1464. [Khim. Geterotsikl. Soedin. 2014, 1590.]

  13. Fozooni, S.; Firoozi, H. Chem. Heterocycl. Compd. 2015, 51, 340. [Khim. Geterotsikl. Soedin. 2015, 51, 340.]

  14. Wang, M.; Zhang, T. T.; Gao, J. J.; Liang, Y. Chem. Heterocycl. Compd. 2012, 48, 897. [Khim. Geterotsikl. Soedin. 2012, 965.]

  15. Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M. Synth. Commun. 2006, 36, 2287.

    Article  CAS  Google Scholar 

  16. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M. A.; Agheb, M.; Heydari, S. Catal. Commun. 2008, 9, 785.

    Article  CAS  Google Scholar 

  17. Wang, L. M.; Hu, L.; Shao, J. H.; Yu, J. J.; Zhang, L. J. Fluorine Chem. 2008, 129, 1139.

    Article  CAS  Google Scholar 

  18. Rostamizadeh, S.; Amani, A. M.; Mahdavinia, G. H.; Sepehrian, H.; Ebrahimi, S. Synthesis 2010, 1356.

  19. Surpur, M. P.; Singh, P. R.; Patil, S. B.; Samant, S. D. Synth. Commun. 2007, 37, 1965.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  21. Baghbanzadeh, M.; Salehi, P.; Dabiri, M.; Kozehgary, G. Synthesis 2006, 344.

  22. Shaterian, H. R.; Oveisi, A. R.; Honarmand, M. Synth. Commun. 2010, 40, 1231.

    Article  CAS  Google Scholar 

  23. Ghashang, M.; Azizi, K.; Moulavi-Pordanjani, H.; Shaterian, H. R. Chin. J. Chem. 2011, 29, 1617.

    Article  Google Scholar 

  24. Yoo, C. L.; Fettinger, J. C.; Kurth, M. J. J. Org. Chem. 2005, 70, 6941.

    Article  CAS  Google Scholar 

  25. Baghbanzadeh, M.; Dabiri, M.; Salehi, P. Heterocycles 2008, 75, 2809.

    Article  CAS  Google Scholar 

  26. Niknam, K.; Mohammadizadeh, M. R.; Mirzaee, S. Chin. J. Chem. 2011, 29, 1417.

    Article  CAS  Google Scholar 

  27. Kassaee, M. Z.; Rostamizadeh, S.; Shadjou, N.; Motamedi, E.; Esmaeelzadeh, M. J. Heterocycl. Chem. 2010, 47, 1421.

    Article  CAS  Google Scholar 

  28. Zhang, Z. H.; Lu, H. Y.; Yang, S. H.; Gao, J. W. J. Comb. Chem. 2010, 12, 643.

    Article  CAS  Google Scholar 

  29. Safari, J.; Gandomi-Ravandi, S. J. Mol. Struct. 2014, 1072, 173.

    Article  CAS  Google Scholar 

  30. Dindulkar, S. D.; Oh, J.; Arole, V. M.; Jeong, Y. T. C. R. Chim. 2014, 17, 971.

    Article  CAS  Google Scholar 

  31. Ghashang, M. Orient. J. Chem. 2012, 28, 1213.

    Article  CAS  Google Scholar 

  32. Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, G.; Mohammadi, A. A. Tetrahedron Lett. 2005, 46, 6123.

    Article  CAS  Google Scholar 

  33. Bharathi, A.; Roopan, S. M.; Kajbafvala, A.; Padmaja, R. D.; Darsana, M. S.; Kumari, G. N. Chin. Chem. Lett. 2014, 25, 324.

    Article  CAS  Google Scholar 

  34. Darvatkar, N. B.; Bhilare, S. V.; Deorukhkar, A. R.; Raut, D. G.; Salunkhe, M. M. Green Chem. Lett. Rev. 2010, 3, 301.

    Article  CAS  Google Scholar 

  35. Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.

    Article  Google Scholar 

  36. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.

    Article  CAS  Google Scholar 

  37. Kumaravel, K.; Vasuki, G. Curr. Org. Chem. 2009, 13, 1820.

    Article  CAS  Google Scholar 

  38. Water in Organic Synthesis; Workbench Edition (Science of Synthesis); Kobayashi, S., Ed.; Thieme: Stuttgart, New York, 2012.

  39. Hailes, H. C. Org. Process Res. Dev. 2007, 11, 114.

    Article  CAS  Google Scholar 

  40. Olyaei, A.; Gesmati, F.; Sadeghpour, M.; Shams, B.; Alizadeh, M. Synth. Commun. 2012, 42, 1650.

    Article  CAS  Google Scholar 

  41. Olyaei, A.; Karbalaei Karimi, M.; Razeghi, R. Tetrahedron Lett. 2013, 54, 5730.

    Article  CAS  Google Scholar 

  42. Olyaei, A., Ghodrat Alidoust, M. Synth. Commun. 2015, 45, 94.

    Article  CAS  Google Scholar 

  43. Karimi-Jaberi, Z.; Arjmandi, R. Monatsh. Chem. 2011, 142, 631.

    Article  CAS  Google Scholar 

  44. Ghorbani-Choghamarani, A.; Taghipour, T. Lett. Org. Chem. 2011, 8, 470.

    Article  CAS  Google Scholar 

  45. Santra, S.; Rahman, Anupam Roy, M.; Majee, A.; Hajra, A. Catal. Commun. 2014, 49, 52.

  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.

    Article  CAS  Google Scholar 

  47. Rostamizadeh, S.; Amani, A. M.; Aryan, R.; Ghaieni, H. R.; Shadjou, N. Synth. Commun. 2008, 38, 3567.

    Article  CAS  Google Scholar 

  48. Niknam, K.; Jafarpour, N.; Niknam, E. Chin. Chem. Lett. 2011, 22, 69.

    Article  CAS  Google Scholar 

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

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Correspondence to Abolfazl Olyaei or Mahdieh Sadeghpour.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 899–902

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Olyaei, A., Rahbarian, F. & Sadeghpour, M. Green and Catalyst-free One-pot Synthesis Of 2,3-dihydroquinazolin-4(1h)-ones in Water. Chem Heterocycl Comp 51, 899–902 (2015). https://doi.org/10.1007/s10593-015-1793-3

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