European Journal of Chemistry

Substituted Quinolinones. Part 16. Preparation and reactions of 3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid

Article Sidebar

PDF
Published: Sep 30, 2011
DOI: https://doi.org/10.5155/eurjchem.2.3.378-387.351
Keywords:
Quinolin-2(1H)-one, b-Keto-carboxylic acid, Pyrano[3, 2-c]quinoline, Knoevenagel condensation, Heterocyclization reactions, Organic synthesis
Section
Research Article
Issue
Vol. 2 No. 3 (2011): September 2011
Dates
Received 2010-11-27
Accepted 2011-01-06
Published 2011-09-30


Main Article Content

Mohamed Abass
Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, 11757, Egypt
Elhossain Ali Mohamed
Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, 11757, Egypt
Mostafa Mohamed Ismail
Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, 11757, Egypt
Aisha Saleh Mayas
Department of Chemistry, Faculty of Education, Sana’a University, Sana’a, Yemen

Abstract

Preparation of quinolinyl-3-oxopropanoic acid was accomplished by hydrolysis of pyranoquinolinedione, in aqueous alkaline medium. The chemical behavior of this β-keto acid towards nitrosation, coupling with a diazonium salt, esterification, condensation with 2,2-diethoxyethanamine, hydrazinolysis, Knoevenagel condensation with isatine, salicylaldehyde, 3-formylquinolones, and 3-formylchromone, was investigated. Also many of the products of these reactions were obtained using either pyranoquinolinedione 1 or β-keto acid 2, under the same conditions.

2_3_378_387_800


icon graph This Abstract was viewed 3646 times | icon graph Article PDF downloaded 1174 times

How to Cite
(1)
Abass, M.; Mohamed, E. A.; Ismail, M. M.; Mayas, A. S. Substituted Quinolinones. Part 16. Preparation and Reactions of 3-(4-Hydroxy-1-Methyl-2-Oxo-1,2-Dihydroquinolin-3-Yl)-3-Oxopropanoic Acid. Eur. J. Chem. 2011, 2, 378-387.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Abass, M.; Mostafa, B. B. Bioorg. Med. Chem. 2005, 13, 6133-6144.
http://dx.doi.org/10.1016/j.bmc.2005.06.038

[2]. El-Shennawy, A. M.; Mohamed, A. H.; Abass M. Gen. Med. J. 2007, 9, 15-33.

[3]. Detsi, A.; Bouloumbasi, D.; Prousis, K. C.; Koufaki, M.; Athanasellis, G.; Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J. Med. Chem. 2007, 50, 2450-2458.
http://dx.doi.org/10.1021/jm061173n
PMid:17444626

[4]. Rivkin, A.; Kim, Y. R.; Goulet, M. T.; Bays, N.; Hill, A. D.; Kariv, I.; Krauss, S.; Ginanni, N.; Strack, P. R.; Kohl, N. E.; Chung, C. C.; Varnerin, J. P.; Goudreau, P. N.; Chang, A.; Tota, M. R.; Munoz, B. Bioorg. Med. Chem. Lett. 2006, 16, 4620-4623.
http://dx.doi.org/10.1016/j.bmcl.2006.06.014

[5]. Tani, M.; Harimaya, K.; Gyobu, Y.; Sasaki, T.; Takennouchi, O.; Kawamura, T.; Kamimura, T.; Harada, T. J. Antibiot. 2004, 57, 89-96.

[6]. Snider, B. B.; Wu X. Heterocycles 2006, 70, 279-294.
http://dx.doi.org/10.3987/COM-06-S(W)20

[7]. Ahvale, A. B.; Prokopcová, H.; Sefcovicova, J.; Steinschifter, W.; Täubl, A. E.; Uray, G.; Stadlbauer, W. Eur. J. Org. Chem. 2008, 563-571.
http://dx.doi.org/10.1002/ejoc.200700855

[8]. Ukrainets, I. V.; Tkach, A. A.; Yang, L. Y. Khim. Geterotsikl. Soedin. 2008, 1655-1663; Chem. Heterocycl. Compds. (Engl. Transl.) 2008, 44, 1347-1354.

[9]. Mohamed, E. A.; Ismail, M. M.; Gabr, Y.; Abass, M.; Farrag, H. A. Indian J. Chem. 1995, 34B, 21-26.

[10]. Mohamed, E. A.; Ismail, M. M.; Gabr, Y.; Abass, M. J. Serb. Chem. Soc. 1993, 58, 737-743.

[11]. Stadlbauer, W.; Badawey, E.; Hojas, G.; Roschger, P.; Kappe T. Molecules 2001, 6, 338-352.
http://dx.doi.org/10.3390/60400338

[12]. Watters, W. H.; Ramachandran, V. N. J. Chem. Research (s) 1997, 184-185, 1201-1215.

[13]. OâDonnell, F.; Smyth, T. J. P.; Ramachandran, V. N.; Smyth, W.F. Inter. J. Antimicrob. Agents 2010, 35, 30-38.
PMid:19748233

[14]. Kammerer, F. J.; Gebert, U.; Alpermann, H. G., U. S. Pat. 1981, US 04 258,046; Chem. Abstr. 1982, 95, 22612s.

[15]. Kappe, T.; Aigner, R.; Hohengassner, P.; Stadlbauer W. J. Prakt Chem. Chem.-Ztg. 1994, 336, 596-601.
http://dx.doi.org/10.1002/prac.19943360707

[16]. Abass, M.; Othman, E. S. Synth. Commun. 2001, 31, 3361-3376.
http://dx.doi.org/10.1081/SCC-100106047

[17]. Mohamed, E. A.; Gabr, Y.; Ismail, M. M.; Abass, M. An. Quim. 1995, 91, 579-584.

[18]. Razzaq, T.; Kappe, C. O. Tetrahedron Lett. 2007, 48, 2513-2517.
http://dx.doi.org/10.1016/j.tetlet.2007.02.052

[19]. Bowman, R. E.; Campbell, A.; Tanner, E. M. J. Org. Chem. 1959, 444-447.

[20]. Bosson, J. A.; Rasmussen, M.; Ritchie, E.; Robertson, A. V.; Taylor, W. C. Australian J. Chem. 1963, 16, 480-490.
http://dx.doi.org/10.1071/CH9630480

[21]. Ibrahim, S. S.; Allimony, H. A.; Othman, E. S. Chem. Papers 1997, 51, 33-42.

[22]. Abass, M.; Ismail, M. M. Chem. Papers 2000, 54, 187-195.

[23]. Mohamed, E. A., Ismail, M. M.; Gabr, Y.; Abass M. Chem. Papers 1994, 48, 285-292.

[24]. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron 1974, 30, 3553-3561.
http://dx.doi.org/10.1016/S0040-4020(01)97034-6

[25]. Abass, M.; Abdel-Megid, M.; Hassan, M. M. Synth. Commun. 2007, 37, 329-352.
http://dx.doi.org/10.1080/00397910601033930

[26]. Kappe, T.; Ajili S.; Stadlbauer, W. J. Heterocycl. Chem. 1988, 25, 463-468.
http://dx.doi.org/10.1002/jhet.5570250221

[27]. Froggett, J. A.; Hockly, M. H.; Titman, R. B. J. Chem. Research (s) 1997, 30-31.

[28]. Jacquot, Y.; Refouvelet, B.; Bermont, L.; Adessi, G. L.; Leclercq, G.; Xicluna, A. Pharmazie 2002, 57, 233-237.
PMid:11998440

[29]. Refouvelet, B.; Guyon, C.; Jacquot, Y.; Girard, C.; Fein, H.; Bévalot, F.; Robert, J. F.; Heyd, B.; Mantion, G.; Richert, L.; Xicluna, A. J. Chem. Soc. 2004, 39, 931-937.

[30]. Alvim, J.; Dias, R. L. A.; Castilho, M. S.; Oliva, G.; Correa, A. G. J. Braz. Chem. Soc. 2005, 16, 763-773.
http://dx.doi.org/10.1590/S0103-50532005000500014

Supporting Agencies

Ain Shams University
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 © 2025 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).