A new series of chromeno[2,3-b]pyridines was efficiently synthesized via chemical transformations of 6-methylchromone-3-carbonitrile with some methylene-active compounds bearing –CH2–CN and –CH2–CO– moieties. Some heteroannelated chromeno[2,3-b]pyridines were also synthesized. The structures of the new synthesized products were deduced on the basis of their analytical and spectral data.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Notes
* Unresolved doublet.
References
R. S. Keri, S. Budagumpi, R. K. Pai, and R. G. Balakrishna, Eur. J. Med. Chem., 78, 340 (2014).
P. Valenti, A. Bisi, A. Rampa, F. Belluti, S. Gobbi, A. Zampiron, and M. Carrara, Bioorg. Med. Chem., 8, 239 (2000).
L.-C. Lim, Y.-C. Kuo, and C.-J. Chou, J. Nat. Prod., 63, 627 (2000).
Y. Q. Shi, T. Fukai, H. Sakagami, W.-J. Chang, P.-Q. Yang, F.-P. Wang, and T. Nomura, J. Nat. Prod., 64, 181 (2001).
W. Huang, Y. Ding, Y. Miao, M.-Z. Liu, Y. Li, and G.-F. Yang, Eur. J. Med. Chem., 44, 3687 (2009).
W. Huang, Q. Chen, W.-C. Yang, and G.-F. Yang, Eur. J. Med. Chem., 66, 161 (2013).
R. Larget, B. Lockhart, P. Renard, and M. Largeron, Bioorg. Med. Chem. Lett., 10, 835 (2000).
J. Ungwitayatorn, W. Samee, and J. Pimthon, J. Mol. Struct., 689, 99 (2004).
T. Ishikava, Y. Oku, T. Tanaka, and T. Kumamoto, Tetrahedron Lett., 40, 3777 (1999).
H. Göker, D. W. Boykin, and S. Yıldız, Bioorg. Med. Chem., 13, 1707 (2005).
Y. Deng, J. P. Lee, M. T. Ramamonjy, J. K. Synder, S. A. Des Etages, D. Kanada, M. P. Synder, and C. J. Turner, J. Nat. Prod., 63, 1082 (2000).
P. J. Pietta, J. Nat. Prod., 63, 1035 (2000).
M. Mazzei, E. Sottofattori, R. Dondero, M. Ibrahim, E. Melloni, and M. Michetti, Farmaco, 53, 452 (1999).
U. Albrecht, M. Lalk, and P. Langer, Bioorg. Med. Chem., 13, 1531 (2005).
G. Singh, R. Singh, N. K. Girdhar, and M. P. S. Ishar, Tetrahedron, 58, 2471 (2002).
C. Chang, C. Wu, S. Kuo, J. Wang, and C. Teng, Chin. Pharm. J., 54, 127 (2002).
A. Nohara, T. Ishiguro, K. Ukawa, H. Sugihara, Y. Maki, and Y. Sanno, J. Med. Chem., 28, 559 (1985).
S.-K. Lee, S.-M. Chae, K.-Y. Yi, N.-J. Kim, and C.-H. Oh, Bull. Korean Chem. Soc., 26, 619 (2005).
K. Ukawa, T. Ishiguro, H. Kurik, and A. Nohara, Chem. Pharm. Bull., 33, 4432 (1985).
S. D. Podos, J. A. Thanassi, and M. J. Pucci, Antimicrob. Agents Chemother., 56, 4095 (2012).
H. M. Hosni and M. M. Abdulla, Acta Pharmaceutica, 58, 175 (2008).
M. A. Ibrahim and N. M. El-Gohary, Heterocycles, 89, 413 (2014).
M. A. Ibrahim, Tetrahedron, 69, 6861 (2013).
M. A. Ibrahim, J. Braz. Chem. Soc., 24, 1754 (2013).
M. A. Ibrahim, T. E. Ali, N. M. El-Gohary, and A. M. El-Kazak, Eur. J. Chem., 4, 311 (2013).
M. A. Ibrahim, T. E. Ali, A. M. El-Kazak, and A. M. Mohamed, Heterocycles, 87, 1075 (2013).
V. Ya. Sosnovskikh, V. S. Moshkin, and M. I. Kodess, Russ. Chem. Bull., Int. Ed., 59, 615 (2010). [Izv. Akad. Nauk, Ser. Khim., 602 (2010).]
V. Ya. Sosnovskikh, V. S. Moshkin, and O. S. El’tsov, Russ. Chem. Bull., Int. Ed., 59, 2151 (2010). [Izv. Akad. Nauk, Ser. Khim., 2097 (2010).]
V. Ya. Sosnovskikh, V. S. Moshkin, and M. I. Kodess, Tetrahedron Lett., 50, 6515 (2009).
V. Ya. Sosnovskikh, V. S. Moshkin, and M. I. Kodess, Tetrahedron Lett., 49, 6856 (2008).
M. A. Ibrahim, ARKIVOC, xvii, 192 (2008).
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1766-1776, November, 2014.
Rights and permissions
About this article
Cite this article
Ibrahim, M.A., El-Gohary, N.M., Ibrahim, S.S. et al. Synthesis of Some Novel Heteroannelated Chromones by Basic Rearrangement of 6-Methylchromone-3-Carbonitrile. Chem Heterocycl Comp 50, 1624–1633 (2015). https://doi.org/10.1007/s10593-014-1632-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1632-y