European Journal of Chemistry 2011, 2(3), 378-387 | doi: https://doi.org/10.5155/eurjchem.2.3.378-387.351 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Mohamed Abass (1,*) , Elhossain Ali Mohamed (2) , Mostafa Mohamed Ismail (3) , Aisha Saleh Mayas (4)

(1) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, 11757, Egypt
(2) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, 11757, Egypt
(3) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, 11757, Egypt
(4) Department of Chemistry, Faculty of Education, Sana’a University, Sana’a, Yemen
(*) Corresponding Author

Received: 27 Nov 2010 | Revised: 05 Jan 2011 | Accepted: 06 Jan 2011 | Published: 30 Sep 2011 | Issue Date: September 2011

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


Keywords


Quinolin-2(1H)-one; b-Keto-carboxylic acid; Pyrano[3,2-c]quinoline; Knoevenagel condensation; Heterocyclization reactions; Organic synthesis

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.3.378-387.351

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 1579 times | PDF Article downloaded 437 times

Funding information


Ain Shams University

Citations

/


[1]. Mohamed Abass, Hassan A. Allimony, Heba Hassan
Substituted Quinolinones. Part 19. New and Unexpected Results from Oxidation of 3-Acetyl-1-Alkyl- 4-Hydroxyquinolin-2(1H)-Ones Using Selenium Dioxide
Phosphorus, Sulfur, and Silicon and the Related Elements  188(12), 1799, 2013
DOI: 10.1080/10426507.2013.787999
/


[2]. Negar Lashgari, Ghodsi Mohammadi Ziarani, Alireza Badiei, Parisa Gholamzadeh
Knoevenagel condensation of isatins with malononitrile/ethyl cyanoacetate in the presence of sulfonic acid functionalized silica (SBA-Pr-SO3H) as a new nano-reactor
European Journal of Chemistry  3(3), 310, 2012
DOI: 10.5155/eurjchem.3.3.310-313.659
/


[3]. Mohamed Abass, El-Hussain A Mohamed, Aisha S Mayas, Akram H Ibrahim
Substituted quinolinones. Part 17: Some nucleophilic reactions with 4-hydroxy-1-methyl-3-[(2-oxo-2H-chromen-3-yl)carbonyl]quinolin-2(1H)-one
Journal of Chemical Sciences  124(5), 1033, 2012
DOI: 10.1007/s12039-012-0303-8
/


[4]. Subrahmanya Ishwar Bhat, Darshak R. Trivedi
A highly efficient and green cascade synthesis of 3-methyl-substituted-4-hydroxy-1-methyl-quinolin-2(1H)-ones under solvent- and catalyst-free conditions
RSC Advances  4(22), 11300, 2014
DOI: 10.1039/c3ra45208e
/


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

How to cite


Abass, M.; Mohamed, E.; Ismail, M.; Mayas, A. Eur. J. Chem. 2011, 2(3), 378-387. doi:10.5155/eurjchem.2.3.378-387.351
Abass, M.; Mohamed, E.; Ismail, M.; Mayas, A. 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(3), 378-387. doi:10.5155/eurjchem.2.3.378-387.351
Abass, M., Mohamed, E., Ismail, M., & Mayas, A. (2011). Substituted Quinolinones. Part 16. Preparation and reactions of 3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid. European Journal of Chemistry, 2(3), 378-387. doi:10.5155/eurjchem.2.3.378-387.351
Abass, Mohamed, Elhossain Ali Mohamed, Mostafa Mohamed Ismail, & Aisha Saleh Mayas. "Substituted Quinolinones. Part 16. Preparation and reactions of 3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid." European Journal of Chemistry [Online], 2.3 (2011): 378-387. Web. 4 Jun. 2020
Abass, Mohamed, Mohamed, Elhossain, Ismail, Mostafa, AND Mayas, Aisha. "Substituted Quinolinones. Part 16. Preparation and reactions of 3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


DOI Link: https://doi.org/10.5155/eurjchem.2.3.378-387.351

| | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2011, 2(3), 378-387 | doi: https://doi.org/10.5155/eurjchem.2.3.378-387.351 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort