European Journal of Chemistry

Synthesis of novel quinazolinone and fused quinazolinones



Main Article Content

Mahmoud Refaee Mahmoud
Manal Mohamed El-Shahawi
Fatma Saber Mohamed Abu El-Azm

Abstract

A number of novel quinazolinone derivatives have been synthesized using the readily obtainable 2-[(1Z,3E)-1-benzamido-4-phenyl-1,3-butadien-1-yl]-3,1-benzoxazin-4(H)one (1) via the reaction with different nitrogen nucleophiles such as azines, Schiff’s base, primary aromatic amines, diamines, hydrazine hydrate and hydroxylamine.

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Mahmoud, M. R.; El-Shahawi, M. M.; Abu El-Azm, F. S. M. Synthesis of Novel Quinazolinone and Fused Quinazolinones. Eur. J. Chem. 2011, 2, 404-409.

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References

[1]. Tang, C.; Chang, S. H.; Hoo, D.; Yanagihara, K. H. Phytochemistry 1975, 14, 2077-2079.
http://dx.doi.org/10.1016/0031-9422(75)83130-X

[2]. Argandona, V. H.; Corcuera, L. J.; Niemeyer, H. M.; Campbell, B. C. Entomol. Exp. Appl. 1983, 34, 134-138.
http://dx.doi.org/10.1111/j.1570-7458.1983.tb03307.x

[3]. Bravo, H. R.; Lazo, W. J. Agric. Food Chem. 1996, 44, 1569-1571.
http://dx.doi.org/10.1021/jf950345e

[4]. Sicker, D.; Frey, M.; Schulz, M.; Gierl, A. Inc. Rev. Cytol. 2000, 198, 319-346.
http://dx.doi.org/10.1016/S0074-7696(00)98008-2

[5]. Macias, F. A.; Marin, D.; Oliveros-Bastidas, A.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. C. J. Agric. Food Chem. 2005, 53, 538-548.
http://dx.doi.org/10.1021/jf0484071
PMid:15686399

[6]. Macias, F. A.; Marin, D.; Oliveros-Bastidas, A.; Chinchilla, D.; Simonet, A. M.; Molinillo, J. M. C. J. Agric. Food Chem. 2006, 54, 991-1000.
http://dx.doi.org/10.1021/jf050896x
PMid:16478208

[7]. Macias, F. A.; Marin, D.; Oliveros-Bastidas, A.; Molinillo, J. M. C. J. Agric. Food Chem. 2006, 54, 9357-9365.
http://dx.doi.org/10.1021/jf062168v
PMid:17147418

[8]. Macias, F. A.; De Siqueira, J. M.; Chinchilla, N.; Marin, D.; Varela, R. M.; Molinillo, J. M. C. J. Agric. Food Chem. 2006, 54, 9843-9851.
http://dx.doi.org/10.1021/jf062709g
PMid:17177510

[9]. Wang, H.; Ganesan A. J. Org. Chem. 2000, 65, 1022â1030.

[10]. Ma, Z.; Hano, Y.; Nomura, T.; Chen, Y. Heterocycles 1997, 46, 541-546.
http://dx.doi.org/10.3987/COM-97-S65

[11]. Raghavendra, N. M.; Thampi, P.; Gurubasavarajaswamy, P. M.; Sriram, D. Archiv der Pharmazi 2007, 340, 635-641.
http://dx.doi.org/10.1002/ardp.200700096
PMid:17994604

[12]. Gao, X.; Cai, X.; Yan, K.; Song, B.; Gao, L.; Chen, Z. Molecules 2007, 12, 2621-2642.
http://dx.doi.org/10.3390/12122621
PMid:18259148

[13]. Pereira, M. D. F.; Chevrot, R.; Rosenfeld, E.; Thiery, V.; Besson, T. J. Enzym. Inhib. Med. Chem. 2007, 22, 577-583.
http://dx.doi.org/10.1080/14756360701425345
PMid:18035826

[14]. Abu-Shady, H. A.; Michael, A. N.; Abbas, S. E.; Abu-Youssef, H. E. Egypt. J. Chem. 2007, 50(3), 313-336.

[15]. Kumar, A.; Rajput, C. B.; Bhati, S. K. Bioorg. Med. Chem. 2007, 15, 3089-3096.
http://dx.doi.org/10.1016/j.bmc.2007.01.042

[16]. Molina, P.; Tarraga, A.; Gonzalez-Tejero, A.; Rioja, I.; Ubeda, A.; Terencio, M. C.; Alcaraz, M. J. J. Nat. Prod. 2001, 64, 1297-1300.
http://dx.doi.org/10.1021/np0101898
PMid:11678654

[17]. de Laszol, S. E.; Quagliato, C. S.; Greenlee, W. J.; Patchett, A. A.; Chang, R. S. L.; Lotti, V. J.; Chen, T. B.; Scheck, S. A.; Faust, K. A.; Kivlign, S. S.; Schorn, T. S.; Zingaro, G. J.; Siegl, P. K. S. J. Med. Chem. 1993, 36, 3207-3210.
http://dx.doi.org/10.1021/jm00073a024
PMid:8230109

[18]. Koizumi, M.; Matsuura, I.; Murakami, Y.; Japan Kokai 77 77, 093, 1977 (C. A. 1978, 88, 6930s).

[19]. Liu, J-F; Ye, P.; Sprague, K.; Sargent, K.; Yohannes, D.; Baldino, C. M.; Wilson, C. J.; Ng, S-C. Org. Lett. 2005, 7, 3363-3366.
http://dx.doi.org/10.1021/ol0513084
PMid:16018661

[20]. El-Gazzar, A. B. A.; Hafez, H. N.; Nawwar, G. A. Eur. J. Med. Chem. 2009, 44, 1427-1436.
http://dx.doi.org/10.1016/j.ejmech.2008.09.030
PMid:18977557

[21]. Witt, A.; Bergman, J. Curr. Org. Chem. 2003, 7, 659-677.
http://dx.doi.org/10.2174/1385272033486738

[22]. Wong, H.; Ganesan, J. J. Org. Chem. 2000, 65, 1022-1030.
http://dx.doi.org/10.1021/jo9914364
PMid:10814050

[23]. Michael, J. P. Nat. Prod. Rep. 2001, 18, 543-559.
http://dx.doi.org/10.1039/b005387m
PMid:11699885

[24]. Dandia, A.; Singh, R. J. Flour. Chem. 2005, 126, 307-312.
http://dx.doi.org/10.1016/j.jfluchem.2004.10.015

[25]. Grover, G.; Kini, S. K. Eur. J. Med. Chem. 2006, 41, 256-262.
http://dx.doi.org/10.1016/j.ejmech.2005.09.002
PMid:16260068

[26]. Reddy, P. S.; Reddy, P. P.; Vasantha, T. Heterocycles 2003, 60, 183-226.
http://dx.doi.org/10.3987/REV-01-540

[27]. Kumar, V.; Mohan, C.; Mahajan, M. P. Tetrahedron 2005, 61, 3533-3538.
http://dx.doi.org/10.1016/j.tet.2005.01.118

[28]. Mahmoud, M. R.; Derbala, H. A. Y. Synth. Commun. 2010, 40, 1516-1529.
http://dx.doi.org/10.1080/00397910903098722

[29]. Rong, Z. Q.; Bai, L. X.; Yan, H. W. Chinese Chem. Lett. 2007, 18(6), 656-658.
http://dx.doi.org/10.1016/j.cclet.2007.04.036

[30]. Ahmed, K.; Shankaraiah, N.; Davaiah, V.; Laxam, R. K. Tetrahedron Lett. 2006, 47(51), 9025-9028.
http://dx.doi.org/10.1016/j.tetlet.2006.10.123

[31]. Moon-Koon, J.; Dong-Su, K.; Hyun, J. L.; Deok-Chan, H.; Young-Dae, G. Tetrahedron Lett. 2005, 46(44), 7477-7481.
http://dx.doi.org/10.1016/j.tetlet.2005.09.015

[32]. Zhixiong, Y.; Yingduo, G.; Raman, K. B.; Meng-Hsin, C.; Susan, P. R.; Scott, D. F.; Sheng-Shung, P.; Andrew, D. H.; Allan, B.; Elizabeth, T. B.; Louis, L.; Rupa, M. P.; Wanda, W. -S. C.; James, M. S., Roy, G. S.; Arthur, A. P.; Ravi, P. N. Bio. Med. Chem. Lett. 2000, 10, 5-8.
http://dx.doi.org/10.1016/S0960-894X(99)00584-3

[33]. Abdullah, G. A.; Robert, S. A.; John, F.; David, R. R. Tetrahedron Lett. 2000, 41(13), 2239-2242.
http://dx.doi.org/10.1016/S0040-4039(00)00138-6

[34]. El-Bassiouny, F. A.; Mahmoud, M. R.; El-Nagdy, S. Asian. J. Chem. 1990, 2, 67-72.

[35]. Ismail, M. F.; Shams, N. A.; Salem, M. R.; Emara, S. A. J. Org. Chem. 1983, 48, 4172-4174.
http://dx.doi.org/10.1021/jo00171a003

[36]. Mahmoud, M. R.; El-Bordany, E. A. A.; Hassan, N. F.; Abu El-Azm, F. S. M. J. Chem. Res. 2007, 9, 541-544.

[37]. Mahmoud, M. R.; El-Shahawi, M. M.; El-Bordany, E. A. A.; Abu El-Azm, F. S. M. Synth. Commun. 2010, 40, 666-676.
http://dx.doi.org/10.1080/00397910903009463

[38]. Mahmoud, M. R.; El-Shahawi, M. M.; El-Bordany, E. A. A.; Abu El-Azm, F. S. M. Eur. J. Chem. 2010, 1(2), 134-139.
http://dx.doi.org/10.5155/eurjchem.1.2.134-139.71

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