European Journal of Chemistry 2010, 1(2), 124-128 | doi: https://doi.org/10.5155/eurjchem.1.2.124-128.75 | Get rights and content

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Synthesis and characterization of new chromeno[2,3-b]pyridines via the Friedländer reactions of 8-allyl-2-amino-4-oxo-4H-chromene-3-carboxaldehyde


Magdy Ahmed Mohamed Ibrahim (1,*)

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

Received: 25 Apr 2010 | Revised: 05 May 2010 | Accepted: 07 May 2010 | Published: 15 Jun 2010 | Issue Date: June 2010

Abstract


New series of chromeno[2,3-b]pyridines, 2-8, have been obtained from 1,8-diazabicyclo [5.4.0]undec-7-ene catalyzed Friedländer reaction of 8-allyl-2-aminochromone-3-carboxaldehyde (1) with some carbonyl compounds containing a reactive α-methyl or methylene group namely 2-acetylthiophene, 3-acetylpyridine, 4-chloroacetophenone, 4,6-diacetylresorcinol, acetylacetone, dibenzoyl methane and acetoacetanilide. Heteroannulated chromones, 13-16, were prepared from Friedländer reaction of 1 with some cyclic α-methylene ketones namely 2-phenyliminothiazolidin-4-one, pyrazoline-3,5-dione, 5,5-dimethylcyclohexane-1,3-dione and thiobarbituric acid. Structures of the newly synthesized compounds have been established from elemental analysis and spectroscopic data.

1_2_124_128_800


Keywords


DBU; Friedländer; Chromeno[2,3-b]pyridine; Heteroannulated chromone

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DOI: 10.5155/eurjchem.1.2.124-128.75

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[1]. Magdy A. Ibrahim, Nasser M. El-Gohary, Sara Said
Synthesis of Heteroannulated Chromeno[2,3-b]Pyridines: DBU Catalyzed Reactions of 2-Amino-6-methylchromone-3-Carboxaldehyde with Some Heterocyclic Enols and Enamines
Journal of Heterocyclic Chemistry  53(1), 117, 2016
DOI: 10.1002/jhet.2285
/

[2]. Naili Luo, Shan Wang, Yue Zhang, Junhu Xin, Cunde Wang
DBU-Promoted Cascade Selective Nucleophilic Addition/C–C Bond Cleavage/Hetero-Diels–Alder Reactions of 2-Amino-4H-chromen-4-ones with β-Nitrostyrenes and/or Aryl Aldehydes: Access to 5H-Chromeno[2,3-b]pyridin-5-ones
The Journal of Organic Chemistry  85(21), 14219, 2020
DOI: 10.1021/acs.joc.0c01993
/

[3]. A.A.M. Farag, Magdy A. Ibrahim, Nasser M. El-Gohary, N. Roushdy
Synthesis and photoelectrical characterizations of ECPPQT for optoelectronic application
Arabian Journal of Chemistry  12(8), 3723, 2019
DOI: 10.1016/j.arabjc.2016.01.002
/

[4]. Magdy A. Ibrahim
Studies on the chemical reactivity of 1H-benzimidazol-2-ylacetonitrile towards some 3-substituted chromones: synthesis of some novel pyrido[1,2-a]benzimidazoles
Tetrahedron  69(33), 6861, 2013
DOI: 10.1016/j.tet.2013.06.011
/

[5]. Shimaa Abdel Halim, Magdy A. Ibrahim
Synthesis, DFT calculations, electronic structure, electronic absorption spectra, natural bond orbital (NBO) and nonlinear optical (NLO) analysis of the novel 5-methyl-8H-benzo[h]chromeno[2,3-b][1,6] naphthyridine-6(5H),8-dione (MBCND)
Journal of Molecular Structure  1130, 543, 2017
DOI: 10.1016/j.molstruc.2016.10.058
/

[6]. Reda M. Abdel-Rahman, Mounir A. I. Salem, Tarik E. Ali, Magdy A. Ibrahim
Utility of 4,6-Diacetylresorcinol in Heterocyclic Synthesis
Chemistry of Heterocyclic Compounds  51(4), 299, 2015
DOI: 10.1007/s10593-015-1699-0
/

[7]. 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
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How to cite


Ibrahim, M. Eur. J. Chem. 2010, 1(2), 124-128. doi:10.5155/eurjchem.1.2.124-128.75
Ibrahim, M. Synthesis and characterization of new chromeno[2,3-b]pyridines via the Friedländer reactions of 8-allyl-2-amino-4-oxo-4H-chromene-3-carboxaldehyde. Eur. J. Chem. 2010, 1(2), 124-128. doi:10.5155/eurjchem.1.2.124-128.75
Ibrahim, M. (2010). Synthesis and characterization of new chromeno[2,3-b]pyridines via the Friedländer reactions of 8-allyl-2-amino-4-oxo-4H-chromene-3-carboxaldehyde. European Journal of Chemistry, 1(2), 124-128. doi:10.5155/eurjchem.1.2.124-128.75
Ibrahim, Magdy. "Synthesis and characterization of new chromeno[2,3-b]pyridines via the Friedländer reactions of 8-allyl-2-amino-4-oxo-4H-chromene-3-carboxaldehyde." European Journal of Chemistry [Online], 1.2 (2010): 124-128. Web. 12 Apr. 2021
Ibrahim, Magdy. "Synthesis and characterization of new chromeno[2,3-b]pyridines via the Friedländer reactions of 8-allyl-2-amino-4-oxo-4H-chromene-3-carboxaldehyde" European Journal of Chemistry [Online], Volume 1 Number 2 (15 June 2010)

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