The Synthesis of Neutral- and Zwitterionic-Ground State Components Containing Binary Chromophore DMABI-IPB-1
2009
Kristīne Teivena, Juris Gulbis, Valdis Kampars

Continuing the investigation of synthesis of the different kind of indan-1,3-dione chomophores for the first time we have synthesized 1-(indan-1,3-dion-2-yl)-4-(2-{N-ethyl-N-[4-(indan-1,3-dion-2-ylidenmethyl)phenyl]amino}ethoxycarbonyl)pyridinium betaine (5), bearing N-(indan-1,3-dion-2-yl)pyridinium betaine (IPB) and 2-(4-N,N-dimethylaminobenzylidene)indan-1,3-dione (DMABI) units connecting by ester bond with yield of 50 % and purity of 99,8 %. Betaine 5 was prepared in three stages – starting with reaction of 4-[N-ethyl-N-(2-hydroxyethyl)amino]benzaldehyde (1) with hydrogenchloride of isonicotinic acid chloranhydride (2) in presence of triethylamine in methylene chloride, further condensation of product 3 with indan-1,3-dione and following reaction to obtained isonicotinic acid 2-{N-ethyl-N-[4-(indan-1,3-dion-2-ylidenemethyl)phenyl]amino}ethyl ester (4) with 2,2-dicyanomethylenindan-1,3-dione oxide. Synthesis of the starting aldehyde 1 also was realized in three steps from N-ethyl-N-(2-hydroxyethyl)aniline. Structure of betaine 5 was proved and confirmed with 1H NMR and masspectroscopy data.


Keywords
1,3-indandione derivatives, pyridinium betainese

Teivena, K., Gulbis, J., Kampars, V. The Synthesis of Neutral- and Zwitterionic-Ground State Components Containing Binary Chromophore DMABI-IPB-1. Materials Sciences and Applied Chemistry. Vol.20, 2009, pp.43-47. ISSN 1407-7353.

Publication language
Latvian (lv)
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