One-Pot Three Component Synthesis of Highly Functionalized Novel 1,8-Naphthyridine Derivatives from Substituted 2-Aminopyridines, Aldehydes and Malononitrile

Muhammad Yaqub; Muhammad Kashif  Naveed; Muhammad Tariq  Riaz; Ruqayia Perveen; Javaria Batool; Nadia Arif; Muhammad Yaseen

doi:10.14233/ajchem.2016.19231

Issue

Vol. 28 No. 1 (2016): Vol 28 Issue 1

Issue Published : October 5, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

One-Pot Three Component Synthesis of Highly Functionalized Novel 1,8-Naphthyridine Derivatives from Substituted 2-Aminopyridines, Aldehydes and Malononitrile

https://doi.org/10.14233/ajchem.2016.19231

Muhammad Yaqub

Institute of Chemical Sciences, Organic Chemistry Division, Bahauddin Zakariya University, Multan-60800, Pakistan

Muhammad Kashif Naveed

Institute of Chemical Sciences, Organic Chemistry Division, Bahauddin Zakariya University, Multan-60800, Pakistan

Muhammad Tariq Riaz

Institute of Chemical Sciences, Organic Chemistry Division, Bahauddin Zakariya University, Multan-60800, Pakistan

Ruqayia Perveen

Institute of Chemical Sciences, Organic Chemistry Division, Bahauddin Zakariya University, Multan-60800, Pakistan

Javaria Batool

Institute of Chemical Sciences, Organic Chemistry Division, Bahauddin Zakariya University, Multan-60800, Pakistan

Nadia Arif

Institute of Chemical Sciences, Organic Chemistry Division, Bahauddin Zakariya University, Multan-60800, Pakistan

Muhammad Yaseen

Mohi-ud-Din Islamic Institute of Pharmaceutical Sciences, Mohi-ud-Din Islamic University, Mirpur, Pakistan

Corresponding Author(s) : Muhammad Yaqub

mayaqub2@yahoo.com

Asian Journal of Chemistry, Vol. 28 No. 1 (2016): Vol 28 Issue 1
Article Published : October 5, 2015

Abstract

Protocol for one-pot three component cascade synthesis was planned to achieve the highly functionalized novel 1,8-naphthyridine derivatives from readily available starting material. Substituted aldehydes and malononitrile were refluxed in THF followed by the addition of substituted 2-aminopyridine to obtain highly functionalized novel 1-8-naphthyridine (12a-12x), in good to excellent yields. The structures of the newly synthesized 1,8-naphthyridine derivatives have been established on the basis of analytical (C, H, N) and spectroscopic (¹H NMR and ¹³C NMR) data. These fully functionalized heterocycles would be employed as versatile synthons for further chemical transformation and eventually, screened for biological studies.

Keywords

Amino acid Ultrasound Aqueous media Cavitation

Yaqub, M., Naveed, M. K. ., Riaz, M. T. ., Perveen, R., Batool, J., Arif, N., & Yaseen, M. (2015). One-Pot Three Component Synthesis of Highly Functionalized Novel 1,8-Naphthyridine Derivatives from Substituted 2-Aminopyridines, Aldehydes and Malononitrile. Asian Journal of Chemistry, 28(1), 69–74. https://doi.org/10.14233/ajchem.2016.19231

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References

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References

L.-R. Wen, C.-Y. Jiang, M. Li and L.-J. Wang, Tetrahedron, 67, 293 (2011); doi:10.1016/j.tet.2010.11.049.

M.A. Seefeld, W.H. Miller, K.A. Newlander, W.J. Burgess, W.E. DeWolf, P.A. Elkins, M.S. Head, D.R. Jakas, C.A. Janson, P.M. Keller, P.J. Manley, T.D. Moore, D.J. Payne, S. Pearson, B.J. Polizzi, X. Qiu, S.F. Rittenhouse, I.N. Uzinskas, N.G. Wallis and W.F. Huffman, J. Med. Chem., 46, 1627 (2003); doi:10.1021/jm0204035.

G. Grossi, M. Di Braccio, G. Roma, V. Ballabeni, M. Tognolini and E. Barocelli, Eur. J. Med. Chem., 40, 155 (2005); doi:10.1016/j.ejmech.2004.09.022.

P.L. Ferrarini, C. Mori, V. Calderone, L. Calzolari, P. Nieri, G. Saccomanni and E. Martinotti, Eur. J. Med. Chem., 34, 505 (1999); doi:10.1016/S0223-5234(99)80099-3.

S.K. Srivastava, M. Jaggi, A.T. Singh, A. Madan, N. Rani, M. Vishnoi, S.K. Agarwal, R. Mukherjee and A.C. Burman, Bioorg. Med. Chem. Lett., 17, 6660 (2007); doi:10.1016/j.bmcl.2007.08.006.

D.C. Adelman, M.J. Evanchik, A. Sudhakar, J.W. Jacobs and J.A. Silverman, 1,8-Naphthyridine Compounds for the Treatment of Cancer, US Patent 8124773 B2 (2012).

Y.J. Hwang. Chung, E.C. Nam, W.T. Kim, J.B. Youm and C.H. Leem, Korean J. Physiol. Pharmacol., 17, 537 (2013); doi:10.4196/kjpp.2013.17.6.537.

G. Grover and S.G. Kini, Eur. J. Med. Chem., 41, 256 (2006); doi:10.1016/j.ejmech.2005.09.002.

S.K. Bouchillon, D.J. Hoban, J.L. Johnson, B.M. Johnson, D.L. Butler, K.A. Saunders, L.A. Miller and J.A. Poupard, Int. J. Antimicrob. Agents, 23, 181 (2004); doi:10.1016/j.ijantimicag.2003.08.006.

P.L. Ferrarini, C. Mori, M. Badawneh, V. Calderone, R. Greco, C. Manera, A. Martinelli, P. Nieri and G. Saccomanni, Eur. J. Med. Chem., 35, 815 (2000); doi:10.1016/S0223-5234(00)00173-2.

A. Samadi, C. Valderas, C. Ríos, A. Bastida, M. Chioua, L. González-Lafuente, I. Colmena, L. Gandía, A. Romero, L. Barrio, M.D. Martín-de-Saavedra, M.G. López, M. Villarroya and J. Marco-Contelles, Bioorg. Med. Chem., 19, 122 (2011); doi:10.1016/j.bmc.2010.11.040.

M. Fischer and A. Bacher, Adv. Bot. Res., 58, 93 (2011); doi:10.1016/B978-0-12-386479-6.00003-2.

M. Yaqub, R. Perveen, Z. Shafiq, H. Pervez and M.N. Tahir, Synlett, 1755 (2012); doi:10.1055/s-0031-1289787.

M. Yaqub, C.-Y. Yu, Y.-M. Jia and Z.-T. Huang, Synlett, 1357 (2008); doi:10.1055/s-2008-1072788.

M. Yaqub, N. Arif, R. Perveen, J. Batool, M.T. Riaz and M. Yaseen, Asian J. Chem., 27, 1013 (2015); doi:10.14233/ajchem.2015.18004.

Issue

Vol. 28 No. 1 (2016): Vol 28 Issue 1

One-Pot Three Component Synthesis of Highly Functionalized Novel 1,8-Naphthyridine Derivatives from Substituted 2-Aminopyridines, Aldehydes and Malononitrile

Corresponding Author(s) : Muhammad Yaqub

Abstract

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