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.

2_3_404_409_800


icon graph This Abstract was viewed 1811 times | icon graph Article PDF downloaded 835 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Supporting Agencies

Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).