European Journal of Chemistry 2011, 2(3), 378-387. doi:10.5155/eurjchem.2.3.378-387.351

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, Accepted: 06 Jan 2011, Published: 30 Sep 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.

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Keywords


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

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DOI: 10.5155/eurjchem.2.3.378-387.351

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Citations

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[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
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[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
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[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
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[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
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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. 19 Nov. 2019
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)

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

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