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



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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Funding information


Faculty of education, Ain Shams university

Citations

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[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‐2 H ‐pyrano[3,2‐ c ]quinoline‐3‐carboxaldehyde
Journal of Heterocyclic Chemistry  , , 2018
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  , 1, 2021
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. 1 Dec. 2021
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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