Novel heterocyclic derivatives of pyrano[3,2-c]quinolinone from  3-(1-ethy1-4-hydroxy-2-oxo-2(1H)-quinolin-3-yl)-3-oxopropanoic acid

Magdy Ahmed Ibrahim; Hany Mohamed Hassanin; Yassin Abdel-Allah Gabr; Youssef Abdel-Salam Alnamer

doi:10.5155/eurjchem.1.3.195-199.91

European Journal of Chemistry 2010, 1(3), 195-199 | doi: https://doi.org/10.5155/eurjchem.1.3.195-199.91 | Get rights and content

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Novel heterocyclic derivatives of pyrano[3,2-c]quinolinone from 3-(1-ethy1-4-hydroxy-2-oxo-2(1H)-quinolin-3-yl)-3-oxopropanoic acid

Magdy Ahmed Ibrahim ^(1,*)

, Hany Mohamed Hassanin ⁽²⁾

, Yassin Abdel-Allah Gabr ⁽³⁾

, Youssef Abdel-Salam Alnamer ⁽⁴⁾

⁽¹⁾ Department of Chemistry, Faculty of Education, Ain Shams University, Roxy 11711, Cairo, Egypt
⁽²⁾ Department of Chemistry, Faculty of Education, Ain Shams University, Roxy 11711, Cairo, Egypt
⁽³⁾ Department of Chemistry, Faculty of Education, Ain Shams University, Roxy 11711, Cairo, Egypt
⁽⁴⁾ Department of Chemistry, Faculty of Education, Ain Shams University, Roxy 11711, Cairo, Egypt
^(*) Corresponding Author

Received: 05 May 2010 | Accepted: 08 Jun 2010 | Published: 29 Sep 2010 | Issue Date: September 2010

Abstract

3-(1-Ethyl-4-hydroxy-2-oxo-2(1H)-quinolin-3-yl)-3-oxopropanoic acid (2) has been synthesized. The chemical behaviour of β-ketoacid 2 was studied towards condensation reactions with salicylaldelyde, 2-hydroxy-1-naphthaldehyde, 1-phenyl-4-hydroxy-2-oxo-quinoline-3-carboxaldehyde, 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxalde-hyde, 2-amino-3-formylchromone and its 8-allyl analog, 3-cyanochromone and its 8-allyl analog. Structures of the newly synthesized products have been deduced from their elemental analysis and spectral data.

1_3_195_199_800

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European Journal of Chemistry

Keywords

β-ketoacid; Quinolinone; Chromone; Cyclocondensation; Knoevenagel condensation

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DOI: 10.5155/eurjchem.1.3.195-199.91

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Faculty of education, Ain Shams university

Citations

[1]. Magdy A. Ibrahim, Hany M. Hassanin, Yassin Gabr, Youssef A. Alnamer
Synthesis and Chemical Reactivity of the Novel 4‐Hydroxy‐6‐methyl‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carboxaldehyde
Journal of Heterocyclic Chemistry 55(12), 2834, 2018
DOI: 10.1002/jhet.3353

[2]. Magdy A. Ibrahim, Hany M. Hassanin
Synthesis and Reactions of the Novel 6‐ethyl‐4‐hydroxy‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carboxaldehyde
Journal of Heterocyclic Chemistry 56(2), 628, 2019
DOI: 10.1002/jhet.3440

[3]. Songlei Zhu, Jing Wang, Zhou Xu, Jie Li
An Efficient One-Pot Synthesis of Pyrano[3,2-c]quinolin-2,5-dione Derivatives Catalyzed by L-Proline
Molecules 17(12), 13856, 2012
DOI: 10.3390/molecules171213856

[4]. Swathi Bandaru, Ravi K. Majji, Satyanarayana Bassa, Pandu N. Chilla, Ramesh Yellapragada, Sruthi Vasamsetty, Rajendra K. Jeldi, Raghu B. Korupolu, Paul D. Sanasi
Magnetic Nano Cobalt Ferrite Catalyzed Synthesis of 4<i>H</i>-Pyrano[3,2-<i>h</i>]quinoline Derivatives under Microwave Irradiation
Green and Sustainable Chemistry 06(02), 101, 2016
DOI: 10.4236/gsc.2016.62009

[5]. Hany M. Hassanin, Magdy A. Ibrahim, Yassin A. Gabr, Youssif A. Alnamer
Synthesis and Chemical Reactivity of Pyrano[3,2‐c]quinolinones
Journal of Heterocyclic Chemistry 49(6), 1269, 2012
DOI: 10.1002/jhet.906

[6]. Shuning Mao, Kaijun Chen, Guobing Yan, Dayun Huang
β‐Keto Acids in Organic Synthesis
European Journal of Organic Chemistry 2020(5), 525, 2020
DOI: 10.1002/ejoc.201901605

[7]. Magdy A. Ibrahim, Adel A.A. Emara, A. Taha, Omima M.I. Adly, A.I. Nabeel, Nesma Salah
Binary and ternary copper(II) complexes with 6-ethyl-4-hydroxy-2,5-dioxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-carboxaldehyde: Synthesis, spectral, thermal, molecular modeling, antimicrobial and antitumor studies
Journal of Molecular Structure 1226, 129358, 2021
DOI: 10.1016/j.molstruc.2020.129358

[8]. Magdy A. Ibrahim, Tarik E. Ali, Azza M. El-Kazak, Amira M. Mohamed
Studies on the Chemical Behavior of the Novel 6,8-Dibromo-7-hydroxychromone-3-carboxaldehyde towards Some Carbon Nucleophilic Reagents
HETEROCYCLES 87(5), 1075, 2013
DOI: 10.3987/COM-13-12709

[9]. Chetan K. Jadhav, Amol S. Nipate, Asha V. Chate, Charansingh. H. Gill
β‐Cyclodextrin: An Efficient Supramolecular Catalyst for the Synthesis of Pyranoquinolines Derivatives under Ultrasonic Irradiation in Water
Polycyclic Aromatic Compounds 42(7), 4224, 2022
DOI: 10.1080/10406638.2021.1886125

[10]. S. S. Shatokhin, V. A. Tuskaev, S. Ch. Gagieva, É. T. Oganesyan
Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone
Russian Chemical Bulletin 70(6), 1011, 2021
DOI: 10.1007/s11172-021-3183-6

[11]. Magdy A. Ibrahim, Nasser M. El-Gohary, Sara Said
Ring Opening Ring Closure Reactions with 3-Substituted Chromones under Nucleophilic Conditions
HETEROCYCLES 91(10), 1863, 2015
DOI: 10.3987/REV-15-824

[12]. Tarik El-Sayed Ali, Magdy Ahmed Ibrahim, Nasser Mohamed El-Gohary, Azza Mohamed El‐Kazak
3-Formylchromones as diverse building blocks in heterocycles synthesis
European Journal of Chemistry 4(3), 311, 2013
DOI: 10.5155/eurjchem.4.3.311-328.815

[13]. Mohammed S. T. Makki, Dina A. Bakhotmah, Reda M. Abdel-Rahman
Highly Efficient Synthesis of Novel Fluorine Bearing Quinoline-4-carboxylic Acid and the Related Compounds as Amylolytic Agents
International Journal of Organic Chemistry 02(01), 49, 2012
DOI: 10.4236/ijoc.2012.21009

[14]. Magdy A. Ibrahim, Hany M. Hassanin, Youssef A. Alnamer
Synthesis, Characterization, and Antimicrobial Evaluation of Some Novel 4-Hydroxyquinolin-2(1H)-ones
Synthetic Communications 44(23), 3470, 2014
DOI: 10.1080/00397911.2014.949775

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How to cite

Ibrahim, M.; Hassanin, H.; Gabr, Y.; Alnamer, Y. Eur. J. Chem. 2010, 1(3), 195-199. doi:10.5155/eurjchem.1.3.195-199.91

Ibrahim, M.; Hassanin, H.; Gabr, Y.; Alnamer, Y. Novel heterocyclic derivatives of pyrano[3,2-c]quinolinone from 3-(1-ethy1-4-hydroxy-2-oxo-2(1H)-quinolin-3-yl)-3-oxopropanoic acid. Eur. J. Chem. 2010, 1(3), 195-199. doi:10.5155/eurjchem.1.3.195-199.91

Ibrahim, M., Hassanin, H., Gabr, Y., & Alnamer, Y. (2010). Novel heterocyclic derivatives of pyrano[3,2-c]quinolinone from 3-(1-ethy1-4-hydroxy-2-oxo-2(1H)-quinolin-3-yl)-3-oxopropanoic acid. European Journal of Chemistry, 1(3), 195-199. doi:10.5155/eurjchem.1.3.195-199.91

Ibrahim, Magdy, Hany Mohamed Hassanin, Yassin Abdel-Allah Gabr, & Youssef Abdel-Salam Alnamer. "Novel heterocyclic derivatives of pyrano[3,2-c]quinolinone from 3-(1-ethy1-4-hydroxy-2-oxo-2(1H)-quinolin-3-yl)-3-oxopropanoic acid." European Journal of Chemistry [Online], 1.3 (2010): 195-199. Web. 30 Nov. 2023

Ibrahim, Magdy, Hassanin, Hany, Gabr, Yassin, AND Alnamer, Youssef. "Novel heterocyclic derivatives of pyrano[3,2-c]quinolinone from 3-(1-ethy1-4-hydroxy-2-oxo-2(1H)-quinolin-3-yl)-3-oxopropanoic acid" European Journal of Chemistry [Online], Volume 1 Number 3 (29 September 2010)

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DOI Link: https://doi.org/10.5155/eurjchem.1.3.195-199.91

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