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Synthesis and Characterization of Some New Dioximes from Various Bisaldehydes and their Transformation to Appropriate Diamines
Corresponding Author(s) : Alireza Banaei
Asian Journal of Chemistry,
Vol. 29 No. 8 (2017): Vol 29 Issue 8
Abstract
In this work, a series of new dioximes (DASOX) 2(a-c) and diamines 3(a-c) derivatives were successfully synthesized. The bisaldehydes 1a was first prepared by reaction of 5-bromo-2-hydroxy benzaldehyde with 2,3-dibromo propanol in the presence of sodium hydroxide in reflux conditions. The reaction of various bisaldehydes 1(a-c) with hydroxylamine hydrochloride in an alcoholic solution in the presence of sodium hydroxide results dioximes 2(a-c) in higher yields. Finally, diamines 3(a-c) was generated by the reduction of dioximes 2(a-c) with LiAlH4 in dry THF. All the newly synthesized compounds characterized by melting point, TLC, elemental analysis, FT-IR, 1H NMR, 13C NMR and Mass spectroscopy.
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- A. Para, Carbohydr. Polym., 57, 277 (2004); https://doi.org/10.1016/j.carbpol.2004.05.005.
- G.L. Kad, M. Bhandari, J. Kaur, R. Rathee and J. Singh, Green Chem., 3, 275 (2001); https://doi.org/10.1039/b107356g.
- A.F. Abdel-Magid, K.G. Carson, B.D. Harris, C.A. Maryanoff and R.D. Shah, J. Org. Chem., 61, 3849 (1996); https://doi.org/10.1021/jo960057x.
- K. Abiraj and D.C. Gowda, J. Chem. Res., 2003, 332 (2003); https://doi.org/10.3184/030823403103174281.
- A.F. Abdel-Magid and S.J. Mehrman, Org. Process Res. Dev., 10, 971 (2006); https://doi.org/10.1021/op0601013.
- D.D. Perrin and W.L.F. Armarego, Purification of Laboratory Chemicals, Pergamon Press, Oxford, edn 3 (1988).
- L.G. Armstrong and I.F. Lindoy, Inorg. Chem., 14, 1322 (1975); https://doi.org/10.1021/ic50148a024.
References
A. Para, Carbohydr. Polym., 57, 277 (2004); https://doi.org/10.1016/j.carbpol.2004.05.005.
G.L. Kad, M. Bhandari, J. Kaur, R. Rathee and J. Singh, Green Chem., 3, 275 (2001); https://doi.org/10.1039/b107356g.
A.F. Abdel-Magid, K.G. Carson, B.D. Harris, C.A. Maryanoff and R.D. Shah, J. Org. Chem., 61, 3849 (1996); https://doi.org/10.1021/jo960057x.
K. Abiraj and D.C. Gowda, J. Chem. Res., 2003, 332 (2003); https://doi.org/10.3184/030823403103174281.
A.F. Abdel-Magid and S.J. Mehrman, Org. Process Res. Dev., 10, 971 (2006); https://doi.org/10.1021/op0601013.
D.D. Perrin and W.L.F. Armarego, Purification of Laboratory Chemicals, Pergamon Press, Oxford, edn 3 (1988).
L.G. Armstrong and I.F. Lindoy, Inorg. Chem., 14, 1322 (1975); https://doi.org/10.1021/ic50148a024.