A new facile synthesis of dimethyl 4-(2-(2,6-bis(methoxycarbonyl)pyridin-4-yl)vinyl) pyridine-2,6-dicarboxylate

Guoliang Gu, Ming Lu

Abstract


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 %.

Keywords


dimethyl 4-(2-(2,6-bis(methoxycarbonyl)pyridin-4-yl)vinyl)pyridine-2,6-dicarboxylate; pyridine dicarboxylic acid derivative; nitrogen base

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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).




DOI: http://dx.doi.org/10.20450/mjcce.2010.163

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