European Journal of Chemistry

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

Article Sidebar

PDF
Published: Jun 15, 2010
DOI: https://doi.org/10.5155/eurjchem.1.2.124-128.75
Keywords:
DBU, Friedländer, Chromeno[2, 3-b]pyridine, Heteroannulated chromone
Section
Research Article
Issue
Vol. 1 No. 2 (2010): June 2010
Dates
Received 2010-04-25
Accepted 2010-05-07
Published 2010-06-15


Main Article Content

Magdy Ahmed Mohamed Ibrahim
Department of Chemistry, Faculty of Education, Ain Shams University, Roxy 11711, Cairo, Egypt

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


icon graph This Abstract was viewed 2408 times | icon graph Article PDF downloaded 1714 times

How to Cite
(1)
Ibrahim, M. A. 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, 124-128.

Article Details

Author Biography

Magdy Ahmed Mohamed Ibrahim, Department of Chemistry, Faculty of Education, Ain Shams University, Roxy 11711, Cairo, Egypt

Department of chemistry, Faculty of Education, Ain Shams University
Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Valenti, P.; Bisi, A.; Rampa, A.; Belluti, F.; Gobbi, S.; Zampiron, A.; Carrara, M. Bioorg. Med. Chem. 2000, 8, 239-246.
doi:10.1016/S0968-0896(99)00282-5

[2]. Lim, L.-C.; Kuo, Y.-C.; Chou, C.-J. J. Nat. Prod. 2000, 63, 627-630.
doi:10.1021/np990538m
PMid:10843573

[3]. Shi, Y. Q.; Fukai, T.; Sakagami, H.; Chang, W.-J.; Yang, P.-Q.; Wang, F.-P.; Nomura, T. J. Nat. Prod. 2001, 64, 181-188.
doi:10.1021/np000317c
PMid:11429996

[4]. Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. Bioorg. Med. Chem. Lett. 2000, 10, 835-838.
doi:10.1016/S0960-894X(00)00110-4

[5]. Ungwitayatorn, J.; Samee, W.; Pimthon, J. J. Mol. Struct. 2004, 689, 99-106.
doi:10.1016/j.molstruc.2003.10.036

[6]. Ishakava, T.; Oku, Y.; Tanaka, T.; Kumamoto, T. Tetrahedron Lett. 1999, 40, 3777-3780.
doi:10.1016/S0040-4039(99)00607-3

[7]. Göker, H.; Boykin, D. W.; Yıldız, S. Bioorg. Med. Chem. 2005, 13, 1707-1714.
doi:10.1016/j.bmc.2004.12.006

[8]. Deng, Y.; Lee, J. P.; Ramamonjy, M. T.; Synder, J. K.; Des Etages, S. A.; Kanada, D.; Synder, M. P.; Turner, C. J. J. Nat. Prod. 2000, 63, 1082-1089.
doi:10.1021/np000054m
PMid:10978202

[9]. Pietta, P. J. J. Nat. Prod. 2000, 63, 1035-1042.
doi:10.1021/np9904509
PMid:10924197

[10]. Mazzei, M.; Sottofattori, E.; Dondero, R.; Ibrahim, M.; Melloni, E.; Michetti, M. Farmaco 1999, 53, 452-460.
doi:10.1016/S0014-827X(99)00051-8

[11]. Albrecht, U.; Lalk, M.; Langer, P. Bioorg. Med. Chem. 2005, 13, 1531-1536.
doi:10.1016/j.bmc.2004.12.031

[12]. Beecher, G. R. J. Nutr. 2003, 133, 3248-3254.

[13]. Oganesyan, E. T.; Tuskayev, V. A.; Sarkisov, L. S. Khim-Farm. Zh. 1994, 28, 17-19.

[14]. Dauzonne, D.; Folléas, B.; Martinez, L.; Chabot, G. G. Eur. J. Med. Chem. 1997, 32, 71-82.
doi:10.1016/S0223-5234(97)84363-2

[15]. Wernar, L.; Norbert, M. J. Heterocycl. Chem. 1996, 33, 943-948.
doi:10.1002/jhet.5570330364

[16]. Wilfried, De N.; Jeffery, E.; Carleen, E.; Nick, S.; Christine, B. N.; Thomas, C. Int. J. Radiat. Oncol. Biol. Phys. 1990, 18, 1359-1365, Chem. Abst. 1991, 114, 20251.

[17]. Singh, G.; Singh, R.; Girdhar, N. K.; Ishar, M. P. S. Tetrahedron 2002, 58, 2471-2480.
doi:10.1016/S0040-4020(02)00128-X

[18]. Chang, C.; Wu, C.; Kuo, S.; Wang, J.; Teng, C. Chin. Pharm. J. 2002, 54, 127-130.

[19]. Ibrahim, S.S.; Allimony, H.A.; Abdel-Halim, A. M.; Ibrahim, M. A. Arkivoc 2009, 14, 28-38.

[20]. Ibrahim, M. A. Tetrahedron 2009, 65, 7687-7690.
doi:10.1016/j.tet.2009.06.107

[21]. Marco-Contelles, J.; Pérez-Mayoral, E.; Samadi, A.; Carreiras, M. D.; Soriano, E. Chem. Rev. 2009, 109, 2652-2671.
doi:10.1021/cr800482c
PMid:19361199

[22]. Yang, D.; Jiang, K.; Li, J.; Xu, F. Tetrahedron 2007, 63, 7654-7658.
doi:10.1016/j.tet.2007.05.037

[23]. Zong, R.;Wang, D.; Hammitt, R.; Thummel, R. P. J. Org. Chem. 2006, 71, 167-175.
doi:10.1021/jo051937r
PMid:16388632

[24]. Emara, A. A. A.; Abou-Hussen, A. A. A. Spectrochim. Acta A 2006, 64, 1010-1024.
doi:10.1016/j.saa.2005.09.010
PMid:16332449

[25]. Muscia, G. C.; Bollini, M.; Carnevale, J. P.; Bruno, A. M.; Asis, S. E. Tetrahedron Lett. 2006, 47, 8811-8815.
doi:10.1016/j.tetlet.2006.10.073

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).