Abstract
A three-component reaction of aromatic aldehyde, naphthalene-2-amine or naphthalen-1-amine, and tert-butyl 2,4-dioxopiperidine-1-carboxylate in reflux EtOH, gave naphtho[1,6]naphthyridine derivatives in high yields under catalyst-free conditions.
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R. Hadj-Slimane, C. Garbay, Pharmaceutical compositions comprising neuropilin inhibitors, and their use for the prevention and/or treatment of angiogenic disorders and cancers, Eur. Pat. Appl. EP 2522341 A1 20121114(2012)
J.W.J. Thuring, Preparation of macrocyclic naphthyridine compounds as integrase inhibitors for use in the treatment of feline immunodeficiency virus, PCT Int. Appl. WO 2012112345 A1 20120823(2012)
D. Barawkar, T. Bende, R. Zahler, A. Bandyopadhyay, R.S. Sarangthem, J. Doshi, Y. Waman, R. Jadhav, U.P. Singh, Preparation of substituted fused tricyclic compounds as JAK kinase inhibitors, compositions and medicinal applications, PCT Int. Appl. WO 2012127506 A1 20120927(2012)
J.-P. Surivet, R. Lange, C. Hubschwerlen, W. Keck, J.-L. Specklin, D. Ritz, D. Bur, H. Locher, P. Seiler, D.S. Strasser, Bioorg. Med. Chem. Lett. 22, 6705 (2012)
N.J. Press, R.J. Taylor, J.D. Fullerton, P. Tranter, C. McCarthy, T.H. Keller, N. Arnold, D. Beer, L. Brown, R. Cheung, J. Med. Chem. 55, 7472 (2012)
N.-E. Haynes, N.R. Scott, L.C. Chen, C.A. Janson, J.K. Li, C.M. Lukacs, A. Railkar, E. Tozzo, T. Whittard, N.F. Brown, ACS Med. Chem. Lett. 3, 764 (2012)
D. Ng, M.P. Arend, L.A. Flippin, Naphthyridine derivatives as inhibitors of hypoxia inducible factor (HIF) hydroxylase and their preparation and use for the treatment of HIF-mediated diseases, PCT Int. Appl. WO 2012106472 A1 20120809(2012)
Y. Sato, Y. Zhang, T. Seino, T. Sugimoto, S. Nishizawa, N. Teramae, Org. Biomol. Chem. 10, 4003 (2012)
F. Pierre, P.C. Chua, S.E. O’Brien, A. Siddiqui-Jain, P. Bourbon, M. Haddach, J. Michaux, J. Nagasawa, M.K. Schwaebe, E. Stefan, J. Med. Chem. 54, 635 (2011)
Y. Zhang, L.P. Quock, E. Chung, Y. Ohgami, R.M. Quock, Eur. J. Pharm. 654, 249 (2011)
S.A. Al-Issa, Molecules 17, 10902 (2012)
M. Li, P. Shao, S.-W. Wang, W. Kong, L.-R. Wen, J. Org. Chem. 77, 8956 (2012)
L. Ali, Z. Hassan, M. Hein, A. Falodun, T. Patonay, A. Villinger, P. Langer, Synthesis 2255 (2012)
A.K. Mailyan, A.S. Peregudov, P.H. Dixneuf, C. Bruneau, S.N. Osipov, J. Org. Chem. 77, 8518 (2012)
S.V. Goswami, P.B. Thorat, B.C. Khade, S.R. Bhusare, Chem. Bio. Inter. 2, 228 (2012)
K.-Y. Wang, C. Chen, J.-F. Liu, Q. Wang, J. Chang, H.-J. Zhu, C. Li, Org. Biomol. Chem. 10, 6693 (2012)
C. Tian, X. Jiao, X. Liu, R. Li, L. Dong, X. Liu, Z. Zhang, J. Xu, M. Xu, P. Xie, Tetrahedron Lett. 53, 4892 (2012)
V. Rustagi, R. Tiwari, A.K. Verma, Eur. J. Org. Chem. 4590–4602 (2012)
N.C. Vijjay, A.U. Rajesh, S. Vinod, A.R. Bindu, J.S. Sreekanth, B. Lakshmi, Acc. Chem. Res. 36, 899 (2003)
L.F. Tietze, Chem. Rev. 96, 115 (1996)
X.S. Wang, M.M. Zhang, Z.S. Zeng, D.Q. Shi, S.J. Tu, X.Y. Wei, Z.M. Zong, Tetrahedron Lett. 46, 7169 (2005)
F. Shi, S. Zhang, S.-S. Wu, Y. Gao, S.J. Tu, Mol. Diversity 15, 497 (2011)
R. Ghorbani-Vaghei, S.M. Malaekehpoor, J. Iran. Chem. Soc. 7, 957 (2010)
S. Chandrasekhar, R.Y. Srinivasa, L. Sreelakshmi, B. Mahipal, C. Raji Reddy, Synthesis. 1737–1740 (2008)
M. Kidwai, S. Rastogi, Heteroatom Chem. 16, 138 (2005)
V. Nadaraj, S.T. Selvi, S. Mohan, Eur. J. Med. Chem. 44, 976 (2009)
X.S. Wang, J. Sheng, L. Lu, K. Yang, Y.L. Li, J. Comb. Chem. 13, 1011 (2011)
X.S. Wang, K. Yang, J. Zhou, S.J. Tu, J. Comb. Chem. 12, 417 (2010)
Acknowledgments
We are grateful to the National Natural Science foundation of China (20802061, 21104064), a Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions, Qing Lan Project (10QLD008, GSFM2011003, 12ssjcxyb05) and College Industrialization Project (JHB2012-31) of Jiangsu Province for financial support.
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Mu, XY., Xu, J., Zhou, YJ. et al. Convenient synthesis of naphtho[1,6] naphthyridine derivatives under catalyst-free conditions. Res Chem Intermed 41, 1703–1714 (2015). https://doi.org/10.1007/s11164-013-1305-y
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DOI: https://doi.org/10.1007/s11164-013-1305-y