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



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Magdy Ahmed Mohamed Ibrahim

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.

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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.

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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
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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

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