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Practical Synthesis of 1,8-Naphthyridine-2,7-dialdehydes Syntone
Corresponding Author(s) : I.I. Levina
Asian Journal of Chemistry,
Vol. 31 No. 11 (2019): Vol 31 Issue 11
Abstract
Several synthetic approaches for synthesizing 1,8-naphthyridines were tested. Reliable protocols for synthesis of some new 1,8-naphthyridine-2,7-dialdehydes were developed starting from 2-amino-6-methylpyridine and acetoacetate. The dialdehyde were found to react with pyrrole to form either a polymer or a macrocycle depending on conditions.
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- D.S. Hecht, I.G. Hu and G. Irvin, Adv. Mater., 23, 1482 (2011); https://doi.org/10.1002/adma.201003188.
- A.A. Gridnev, eds.: A.C.F. Ribeiro, C.I A.V. Santos and G.E. Zaikov, Polynuclear Chelates with Tunable Aromaticity of Macrocyclic Equatorial Ligand, In: Chemical Analysis: Modern Materials Evaluation and Testing Methods, CRC Press, Chap. 8, pp. 131-141 (2016).
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- M.A. Hussein, M.A. Abdel-Rahman and A.A. Geies, J. Appl. Polym. Sci., 126, 2 (2012); https://doi.org/10.1002/app.36395.
- C. Vu, D. Walker, J. Wells and S. Fox, J. Heterocycl. Chem., 39, 829 (2002); https://doi.org/10.1002/jhet.5570390432.
- C.J. Chandler, L.W. Deady, J.A. Reiss and V.J. Tzimos, Heterocycl. Chem., 19, 1017 (1982); https://doi.org/10.1002/jhet.5570190507.
- O. Seide, J. Liebigs Ann. Chem., 440, 311 (1924); https://doi.org/10.1002/jlac.19244400127.
- O. Seide, Chem. Ber., 59, 2465 (1926); https://doi.org/10.1002/cber.19260591007.
- K.R. Reddy, R. Mogilaiah and B. Sreenivasulu, Indian J. Chem., 28B, 362 (1989).
- K. Mogilaiah and S.N.V. Reddy, Indian J. Chem., 41B, 215 (2002).
- J. Turner, J. Org. Chem., 48, 3401 (1983); https://doi.org/10.1021/jo00168a007.
- M.Y. Saleh and A.I. Ayoub, Eur. J. Chem., 5, 475 (2014); https://doi.org/10.5155/eurjchem.5.3.475-480.1050.
- E.V. Brown, J. Org. Chem., 30, 1607 (1965); https://doi.org/10.1021/jo01016a066.
References
D.S. Hecht, I.G. Hu and G. Irvin, Adv. Mater., 23, 1482 (2011); https://doi.org/10.1002/adma.201003188.
A.A. Gridnev, eds.: A.C.F. Ribeiro, C.I A.V. Santos and G.E. Zaikov, Polynuclear Chelates with Tunable Aromaticity of Macrocyclic Equatorial Ligand, In: Chemical Analysis: Modern Materials Evaluation and Testing Methods, CRC Press, Chap. 8, pp. 131-141 (2016).
T.J. Cardwell, R.W. Cattrall, L.W. Deady, K.L. Murphy and S.S. Tan, Aust. J. Chem., 45, 983 (1992); https://doi.org/10.1071/CH9920983.
S. Goswami, R. Mukherjee, R. Mukherjee, S. Jana, A. Maity and A. Adak, Molecules, 10, 929 (2005); https://doi.org/10.3390/10080929.
M.A. Hussein, M.A. Abdel-Rahman and A.A. Geies, J. Appl. Polym. Sci., 126, 2 (2012); https://doi.org/10.1002/app.36395.
C. Vu, D. Walker, J. Wells and S. Fox, J. Heterocycl. Chem., 39, 829 (2002); https://doi.org/10.1002/jhet.5570390432.
C.J. Chandler, L.W. Deady, J.A. Reiss and V.J. Tzimos, Heterocycl. Chem., 19, 1017 (1982); https://doi.org/10.1002/jhet.5570190507.
O. Seide, J. Liebigs Ann. Chem., 440, 311 (1924); https://doi.org/10.1002/jlac.19244400127.
O. Seide, Chem. Ber., 59, 2465 (1926); https://doi.org/10.1002/cber.19260591007.
K.R. Reddy, R. Mogilaiah and B. Sreenivasulu, Indian J. Chem., 28B, 362 (1989).
K. Mogilaiah and S.N.V. Reddy, Indian J. Chem., 41B, 215 (2002).
J. Turner, J. Org. Chem., 48, 3401 (1983); https://doi.org/10.1021/jo00168a007.
M.Y. Saleh and A.I. Ayoub, Eur. J. Chem., 5, 475 (2014); https://doi.org/10.5155/eurjchem.5.3.475-480.1050.
E.V. Brown, J. Org. Chem., 30, 1607 (1965); https://doi.org/10.1021/jo01016a066.