European Journal of Chemistry 2011, 2(3), 404-409 | doi: https://doi.org/10.5155/eurjchem.2.3.404-409.267 | Get rights and content

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Synthesis of novel quinazolinone and fused quinazolinones


Mahmoud Refaee Mahmoud (1) , Manal Mohamed El-Shahawi (2) , Fatma Saber Mohamed Abu El-Azm (3,*)

(1) Chemistry Department, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt
(2) Chemistry Department, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt
(3) Chemistry Department, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt
(*) Corresponding Author

Received: 28 Aug 2010 | Accepted: 04 Jan 2011 | Published: 30 Sep 2011 | Issue Date: September 2011

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.

2_3_404_409_800


Keywords


Benzoxazinone; Azine; Fused quinazolinones; Nitrogen nucleophiles; Triazinoquinazolinone; Oxadiazinoquinazolinone

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DOI: 10.5155/eurjchem.2.3.404-409.267

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Citations

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[1]. M.R. Mahmoud, F.S.M. Abu El-Azm
Synthesis and Spectral Study of Novel Benzopyrone and Quinolinone Derivatives
Journal of Chemical Research  37(9), 535, 2013
DOI: 10.3184/174751913X13738962423671
/


[2]. Manal M. Elshahawi, Ahmed K. EL-Ziaty, Jehan M. Morsy, Aly F. Aly
Synthesis and Insecticidal Efficacy of Novel Bis Quinazolinone Derivatives
Journal of Heterocyclic Chemistry  53(5), 1443, 2016
DOI: 10.1002/jhet.2445
/


[3]. Mohamed H. Hekal, Fatma S. M. Abu El-Azm
New potential antitumor quinazolinones derived from dynamic 2-undecyl benzoxazinone: Synthesis and cytotoxic evaluation
Synthetic Communications  48(18), 2391, 2018
DOI: 10.1080/00397911.2018.1490433
/


[4]. Mahmoud R. Mahmoud, Ahmed K. El-Ziaty, Fatma S. M. Abu El-Azm, Mahmoud F. Ismail, Sayed A. Shiba
Utility of Cyano-N-(2-oxo-1,2-dihydroindol-3-ylidene)acetohydrazide in the Synthesis of Novel Heterocycles
Journal of Chemical Research  37(2), 80, 2013
DOI: 10.3184/174751912X13567100793191
/


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


How to cite


Mahmoud, M.; El-Shahawi, M.; Abu El-Azm, F. Eur. J. Chem. 2011, 2(3), 404-409. doi:10.5155/eurjchem.2.3.404-409.267
Mahmoud, M.; El-Shahawi, M.; Abu El-Azm, F. Synthesis of novel quinazolinone and fused quinazolinones. Eur. J. Chem. 2011, 2(3), 404-409. doi:10.5155/eurjchem.2.3.404-409.267
Mahmoud, M., El-Shahawi, M., & Abu El-Azm, F. (2011). Synthesis of novel quinazolinone and fused quinazolinones. European Journal of Chemistry, 2(3), 404-409. doi:10.5155/eurjchem.2.3.404-409.267
Mahmoud, Mahmoud, Manal Mohamed El-Shahawi, & Fatma Saber Mohamed Abu El-Azm. "Synthesis of novel quinazolinone and fused quinazolinones." European Journal of Chemistry [Online], 2.3 (2011): 404-409. Web. 24 Oct. 2021
Mahmoud, Mahmoud, El-Shahawi, Manal, AND Abu El-Azm, Fatma. "Synthesis of novel quinazolinone and fused quinazolinones" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

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