2014年11月
Quinolone Analogs 13: Synthesis of Novel 1,1 '-(2-Methylenepropane-1,3-diyl)di(4-quinolone-3-carboxylate) and Related Compounds
JOURNAL OF HETEROCYCLIC CHEMISTRY
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- 巻
- 51
- 号
- 6
- 開始ページ
- 1720
- 終了ページ
- 1726
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1002/jhet.1861
- 出版者・発行元
- WILEY-BLACKWELL
The reaction of the 4-hydroxyquinoline-3-carboxylate 6 with pentaerythritol tribromide gave the 1,1-(2-methylenepropane-1,3-diyl)di(4-quinolone-3-carboxylate) 11, whose reaction with bromine afforded the 1,1-(2-bromo-2-bromomethylpropane-1,3-diyl)di(4-quinolone-3-carboxylate) 12. Compound 12 was transformed into the (Z)-1,1-(2-acetoxymethylpropene-1,3-diyl)di(4-quinolone-3-carboxylate) 13 or (E)-1,1-[2-(imidazol-1-ylmethyl)propene-1,3-diyl]di(4-quinolone-3-carboxylate) 14. Hydrolysis of the dimer (Z)-13 or (E)-14 with potassium hydroxide provided the (E)-1,1-(2-hydroxymethylpropene-1,3-diyl)di(4-quinolone-3-carboxylic acid) 15 or (Z)-1,1-[2-(imidazol-1-ylmethyl)propene-1,3-diyl]di(4-quinolone-3-carboxylic acid) 16, respectively. The nuclear Overhauser effect (NOE) spectral data supported that those hydrolysis resulted in the geometrical conversion of (Z)-13 into (E)-15 or (E)-14 into (Z)-16.
- リンク情報
- ID情報
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- DOI : 10.1002/jhet.1861
- ISSN : 0022-152X
- eISSN : 1943-5193
- Web of Science ID : WOS:000345457700021