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; Elhossain Ali Mohamed; Mostafa Mohamed Ismail; Aisha Saleh Mayas

doi:10.5155/eurjchem.2.3.378-387.351

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

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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.

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European Journal of Chemistry

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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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

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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. 4 Jun. 2023

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)

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

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