2,3-Dihydroquinazolin-4(1H)-one derivatives were synthesized via a one-pot, three-component reaction of isatoic anhydride and an aromatic aldehyde with 4-aminohippuric acid, catalyzed by acetic acid. After completion of the reaction, the corresponding products were reacted with an aromatic aldehyde, acetic anhydride, and sodium acetate to yield oxazolone derivatives. The reactions were carried out under microwave irradiation and reflux.
Similar content being viewed by others
References
(a) Kappe, T.; Stadlbauer, W. In Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, J. Eds.; Academic Press: New York, 1981, vol. 28, p. 127. (b) Pummerer, R.; Fiesselmann, H.; Muller, O. Justus Liebigs Ann. Chem. 1940, 544, 206. (c) Harris, F.; Lopez, M. J. Appl. Polym. Sci. 1993, 50, 559. (d) Miyamae, T. Microbiol. Immunol. 1996, 40, 761.
(a) Coppola, G. M. Synthesis 1980, 7, 505. (b) Ren, J.; Goss, D. J. Nucleic Acids Res. 1996, 24, 3629. (c) Nawrot, B.; Milius, W.; Ejchart, A.; Limmer, St.; Sprinzl, M. Nucleic Acids Res. 1997, 25, 948.
(a) Sadanadam, Y. S.; Ram Mohan Reddy, K.; Bhaskar Rao, A. Eur. J. Med. Chem. 1987, 22, 169. (b) Yale, H. L.; Kalkstein, M.J. Med. Chem. 1967, 10, 334. (c) Bonola, G.; Sianesi, E. J. Med. Chem. 1970, 13, 329. (d) 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. (e) Gupta, R. C.; Nath, R.; Shanker, K.; Bhargava, K. P.; Kishore, K. J. Indian Chem. Soc. 1979, 56, 219. (f) Davoodnia, A.; Bakavoli, M.; Khorramdelan, F.; Roshani, M. Indian J. Heterocycl. Chem. 2006, 16, 147.
(a) Sharma, S. D.; Kaur, V. Synthesis 1989, 677. (b) Moore, J. A.; Sutherland, G. J.; Sowerby, R.; Kelly, E. J.; Palermo, W. W. J. Org. Chem. 1969, 34, 887. (c) Qiao, R. Z.; Xu, B. L.; Wang, Y. H. Chin. Chem. Lett. 2007, 18, 656. (d) Magyar, T.; Miklós, F.; Lázár, L.; Fülöp, F. Chem. Heterocycl. Compd. 2015, 50, 1464. [Khim. Geterotsikl. Soedin. 2014, 1590.]
(a) Su, W.; Yang, B. Aust. J. Chem. 2002, 55, 695. (b) Shi, D.; Rong, L.; Wang, J.; Zhuang, Q.; Wang, X.; Hu, H. Tetrahedron Lett. 2003, 44, 3199.
Mieriņa, I.; Tetere, Z.; Zicāne, D.; Rāviņa, I.; Turks, M.; Jure, M. Chem. Heterocycl. Compd. 2013, 48, 1824. [Khim. Geterotsikl. Soedin. 2013, 1948.]
Baghbanzadeh, M.; Salehi, P. Dabiri, M.; Kozehgary, G. Synthesis 2006, 344.
Surpur, M. P.; Singh, P. R.; Patil, S. B.; Samant, S. D. Synth. Commun. 2007, 37, 1965.
Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M. Synth. Commun. 2006, 36, 2287.
Dabiri, M.; Salehi, P.; Baghbanzadeh, M. Monatsh. Chem. 2007, 138, 1191.
(a) Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M. A.; Agheb, M.; Hedari, S. Catal. Commun. 2008, 9, 785. (b) Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Baghbanzadeh, M. Tetrahedron Lett. 2005, 46, 7051.
Wang, L. M.; Hu, L.; Shao, J. H.; Yu, J. J.; Zhang, L. J. Fluorine Chem. 2008, 129, 1139.
Baghbanzadeh, M.; Dabiri, M.; Salehi, P. Heterocycles 2008, 75, 2809.
Aaglawe, M. J.; Dhule, S. S.; Bahekar, S. S.; Wakte, P. S.; Shinde, D. B. J. Korean Chem. Soc. 2003, 47, 133.
Benededetti-Doctorovich, V; Burgess, E. M.; Lambropoulos, J.; Lednicer, D.; Van Derveer, D.; Zalkow, L. J. Med. Chem. 1994, 37, 710.
(a) Rodrigues Pereira, E.; Sancelme, M.; Voldoire, A.; Prudhomme, M. Bioorg. Med. Chem. Lett. 1997, 7, 2503. (b) Viti, G.; Namnicini, R.; Ricci, R.; Pestellini, V.; Abelli, L.; Furio, M. Eur. J. Med. Chem. 1994, 29, 401.
(a) Gottwald, K.; Seebach, D. Tetrahedron 1999, 55, 723. (b) Meiwes, J.; Schudock, M.; Kretzschmar, G. Tetrahedron: Asymmetry 1997, 8, 527. (c) Seebach, D.; Jaeschke, G.; Gottwald, K.; Matsuda, K.; Formisano, R.; Chaplin, D. A.; Breuning, M.; Bringmann, G. Tetrahedron 1997, 53, 7539. (d) Cativiela, C.; Díaz-de-Villegas, M. D.; García, J. I.; Jiménez, A. I. Tetrahedron 1997, 53, 4479. (e) Buñuel, E.; Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron 1995, 51, 8923. (f) Donati, D.; Garzon-Aburbeh, A.; Natalini, B.; Marchioro, C.; Pellicciari, R. Tetrahedron 1996, 52, 9901.
(a) Martinez, A. P.; Lee, W. W.; Goodman, L. Tetrahedron 1964, 20, 2763. (b) Gelmi, M. L.; Clerici, F.; Melis, A. Tetrahedron 1997, 53, 1843. (c) Mesaik, M. A.; Rahat, S.; Khan, K. M.; Zia-Ullah; Choudhary, M. I.; Murad, S.; Ismail, Z.; Atta-ur-Rahman; Ahmad, A. Bioorg. Med. Chem. 2004, 12, 2049.
Fozooni, S.; Tikdari, A. M.; Hamidian, H.; Khabazzadeh, H. ARKIVOC 2008, (xiv), 115.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(4), 340–345
Rights and permissions
About this article
Cite this article
Fozooni, S., Firoozi, H. Microwave-Assisted Synthesis of New Quinazolinone and (dihydroquinazolinylphenyl)oxazolone Derivatives. Chem Heterocycl Comp 51, 340–345 (2015). https://doi.org/10.1007/s10593-015-1705-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-015-1705-6