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Synthesis of 7,8‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐2 H ‐chromen‐2‐one derivatives of crown ethers
Author(s) -
Gündüz Cihan,
Bulut Mustafa
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.17
Subject(s) - chemistry , sodium hydroxide , acrylonitrile , pyridine , hydrochloride , demethylation , nuclear chemistry , alkali metal , aqueous solution , organic chemistry , potassium hydroxide , sodium ethoxide , proton nmr , salt (chemistry) , ethanol , medicinal chemistry , dna methylation , gene , biochemistry , gene expression , copolymer , polymer
The novel 1‐(3,4‐dimethoxyphenyl)‐2‐(2,3,4‐trimethoxyphenyl)acrylonitrile was prepared from the condensation of the mixture of 2,3,4‐trimethoxybenzaldehyde and 3,4‐dimethoxyphenylacetonitrile in ethanol at 70°C with 20% aqueous sodium hydroxide solution. Cyclization and demethylation of the acrylacetonitrile was performed using pyridine hydrochloride. The obtained 7,8‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐2 H ‐chromen‐2‐one was reacted with the poly(ethylene glycol) ditosylates in CH 3 CN/alkali carbonate to afford bis‐[12]crown‐4, ‐[15]crown‐5, and ‐[18]crown‐6 chromenones. The chromatographically purified novel chromenone crown ethers were identified by IR, 1 H NMR, 13 C NMR, and MALDI‐TOF mass spectrometry and elemental analysis. J. Heterocyclic Chem., (2009).