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.
Similar content being viewed by others
References
Cox, R. J.; O'Hagan, D. J. Chem. Soc. Perkin, Trans. 1 1991, 1, 2537.
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.
El-Sabbagh, O. I.; Ibrahim, S. M.; Baraka, M. M.; Kothayer, H. Arch. Pharm. 2010, 343, 274.
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.
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.
Alaimo, R. J.; Russell, H. E. J. Med. Chem. 1972, 15, 335.
White, D. C.; Greenwood, T. D.; Downey, A. L.; Bloomquist, J. R.; Wolfe, J. F. Bioorg. Med. Chem. 2004, 12, 5711.
Abdel-Jalil, R. J.; Volter, W.; Saeed, M. Tetrahedron Lett. 2004, 45, 3475.
Lopez, S. E.; Rosales, M. E.; Urdaneta, N.; Godoy, M. V.; Charris, J. E. J. Chem. Res. 2000, 258.
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.
Liu, J. F.; Lee, J.; Dalton, A. M.; Bi, G.; Yu, L.; Baldino, C. M.; McElory, E.; Brown, M. Tetrahedron Lett. 2005, 46, 1241.
Magyar, T.; Miklós, F.; Lázár, L.; Fülöp, F. Chem. Heterocycl. Compd. 2015, 50, 1464. [Khim. Geterotsikl. Soedin. 2014, 1590.]
Fozooni, S.; Firoozi, H. Chem. Heterocycl. Compd. 2015, 51, 340. [Khim. Geterotsikl. Soedin. 2015, 51, 340.]
Wang, M.; Zhang, T. T.; Gao, J. J.; Liang, Y. Chem. Heterocycl. Compd. 2012, 48, 897. [Khim. Geterotsikl. Soedin. 2012, 965.]
Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M. Synth. Commun. 2006, 36, 2287.
Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M. A.; Agheb, M.; Heydari, S. Catal. Commun. 2008, 9, 785.
Wang, L. M.; Hu, L.; Shao, J. H.; Yu, J. J.; Zhang, L. J. Fluorine Chem. 2008, 129, 1139.
Rostamizadeh, S.; Amani, A. M.; Mahdavinia, G. H.; Sepehrian, H.; Ebrahimi, S. Synthesis 2010, 1356.
Surpur, M. P.; Singh, P. R.; Patil, S. B.; Samant, S. D. Synth. Commun. 2007, 37, 1965.
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.
Baghbanzadeh, M.; Salehi, P.; Dabiri, M.; Kozehgary, G. Synthesis 2006, 344.
Shaterian, H. R.; Oveisi, A. R.; Honarmand, M. Synth. Commun. 2010, 40, 1231.
Ghashang, M.; Azizi, K.; Moulavi-Pordanjani, H.; Shaterian, H. R. Chin. J. Chem. 2011, 29, 1617.
Yoo, C. L.; Fettinger, J. C.; Kurth, M. J. J. Org. Chem. 2005, 70, 6941.
Baghbanzadeh, M.; Dabiri, M.; Salehi, P. Heterocycles 2008, 75, 2809.
Niknam, K.; Mohammadizadeh, M. R.; Mirzaee, S. Chin. J. Chem. 2011, 29, 1417.
Kassaee, M. Z.; Rostamizadeh, S.; Shadjou, N.; Motamedi, E.; Esmaeelzadeh, M. J. Heterocycl. Chem. 2010, 47, 1421.
Zhang, Z. H.; Lu, H. Y.; Yang, S. H.; Gao, J. W. J. Comb. Chem. 2010, 12, 643.
Safari, J.; Gandomi-Ravandi, S. J. Mol. Struct. 2014, 1072, 173.
Dindulkar, S. D.; Oh, J.; Arole, V. M.; Jeong, Y. T. C. R. Chim. 2014, 17, 971.
Ghashang, M. Orient. J. Chem. 2012, 28, 1213.
Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, G.; Mohammadi, A. A. Tetrahedron Lett. 2005, 46, 6123.
Bharathi, A.; Roopan, S. M.; Kajbafvala, A.; Padmaja, R. D.; Darsana, M. S.; Kumari, G. N. Chin. Chem. Lett. 2014, 25, 324.
Darvatkar, N. B.; Bhilare, S. V.; Deorukhkar, A. R.; Raut, D. G.; Salunkhe, M. M. Green Chem. Lett. Rev. 2010, 3, 301.
Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.
Kumaravel, K.; Vasuki, G. Curr. Org. Chem. 2009, 13, 1820.
Water in Organic Synthesis; Workbench Edition (Science of Synthesis); Kobayashi, S., Ed.; Thieme: Stuttgart, New York, 2012.
Hailes, H. C. Org. Process Res. Dev. 2007, 11, 114.
Olyaei, A.; Gesmati, F.; Sadeghpour, M.; Shams, B.; Alizadeh, M. Synth. Commun. 2012, 42, 1650.
Olyaei, A.; Karbalaei Karimi, M.; Razeghi, R. Tetrahedron Lett. 2013, 54, 5730.
Olyaei, A., Ghodrat Alidoust, M. Synth. Commun. 2015, 45, 94.
Karimi-Jaberi, Z.; Arjmandi, R. Monatsh. Chem. 2011, 142, 631.
Ghorbani-Choghamarani, A.; Taghipour, T. Lett. Org. Chem. 2011, 8, 470.
Santra, S.; Rahman, Anupam Roy, M.; Majee, A.; Hajra, A. Catal. Commun. 2014, 49, 52.
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.
Rostamizadeh, S.; Amani, A. M.; Aryan, R.; Ghaieni, H. R.; Shadjou, N. Synth. Commun. 2008, 38, 3567.
Niknam, K.; Jafarpour, N.; Niknam, E. Chin. Chem. Lett. 2011, 22, 69.
The authors thank the Research Council of Payame Noor University for financial support.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 899–902
Rights and permissions
About this article
Cite this article
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
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-015-1793-3