A new facile synthesis of dimethyl 4-(2-(2,6-bis(methoxycarbonyl)pyridin-4-yl)vinyl) pyridine-2,6-dicarboxylate
DOI:
https://doi.org/10.20450/mjcce.2010.163Keywords:
dimethyl 4-(2-(2, 6-bis(methoxycarbonyl)pyridin-4-yl)vinyl)pyridine-2, 6-dicarboxylate, pyridine dicarboxylic acid derivative, nitrogen baseAbstract
A new facile synthesis of pyridine dicarboxylic acid derivative, dimethyl 4-(2-(2,6-bis(methoxycarbonyl)pyridin-4-yl)vinyl)pyridine-2,6-dicarboxylate (DVDPA), from dimethyl 4-(chloromethyl)pyridine-2,6-dicarboxylate (CMDPA) in presence of nitrogen bases has been described. The influences of different base/CMDPA molar ratio and different nitrogen bases were also investigated. The result has shown that the yield could reach 81 % when triethylamine was used and the molar ratio of base/CMDPA was 2.4. The overall yield of title compound via the three-step synthesis starting from dimethyl 4-(hydroxylmethyl)pyridine-2,6-dicarboxylate (HMDPA) was improved to 69 %.References
Paul N.W., Synthesis and properties of a twistophane
ion sensor: A new conjugated macrocyclic
ligand for the spectroscopic detection of metal ions,
J. Org. Chem., 66, 4170–4179 (2001).
Y. Hasegawa, Y. Wada, S. Yanagida, Strategies for
the design of luminescent lanthanide(III) complexes
and their photonic applications, J. Photochem.
Photobiol. C: Photochem. Rev., 5, 183–202 (2004).
P. Gawryszewska, J. Sokolnicki, J. Legendziewicz,
Photophysics and structure of selected lanthanide compounds.
Coord. Chem. Rev., 249, 2489–2509 (2005).
I. Hemmila, V. Laitala, Progress in lanthanides as luminescent
probes. J. Fluoresc., 15, 529–542 (2005).
J. C. G. Bunzli, Benefiting from the unique properties
of lanthanide ions. Acc. Chem. Res., 39, 53–61 (2006).
M. Morita, D. Rau, M. Herren, Circularly polarized
luminescence and enantiomeric energy transfer discrimination
of chiral Tb(III)–Nd(III) EDDS and related
complexes. J. Alloys Compd., 380, 260–267 (2004).
J. Sokolnicki, J. Legendziewicz, G. Muller and J. P.
Riehl, The luminescence, molecular and electronic
structure, and excited state energetics of tris complexes
of 4-phenylethynyl-2,6-pyridinedicarboxylic
acid with Eu(III) and Tb(III) prepared in sol–gel,
Opt. Mater., 27, 1529–1536 (2005).
G. L Gu, R. R. Tang, Y. H. Zheng and X. M. Shi,
Synthesis, characterization and fluorescence properties
of novel pyridine dicarboxylic acid derivatives
and corresponding Tb(III) complexes, Spectrochim.
Acta. Part A., 71, 209–214 (2008).
G. P. Sollott, Conversion of 2,4,6-trinitrobenzyl chloride
to. 2,2′,4,4′,6,6′ -hexanitrostilbene by nitrogen
bases, J. Org. Chem., 47, 2471–2474 (1982)
R. R. Tang, Y. H. Zheng, G.L Gu, Synthesis and
fluorescence properties of Tb(III) complexes with
pyridine-2,6-dicarboxylic acid derivatives, J.
Cent. South Univ. Technol., 15, 599–605 (2008).
R.R. Tang, Y. H. Zheng, Q. Zhao, Synthesis of Dimethyl
-(hydroxymethyl)pyridine-2, 6-dicarboxylate.
Chem. React. Eng. Techno., 22, 83–85 (2006).
Downloads
Published
How to Cite
Issue
Section
License
The authors agree to the following licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)
- Share — copy and redistribute the material in any medium or format
- Adapt — remix, transform, and build upon the material
- for any purpose, even commercially.
Under the following terms:
Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
- NonCommercial — You may not use the material for commercial purposes.