Quinolone analogs 13: Synthesis of novel 1,1′-(2-methylenepropane-1,3-diyl)di(4-quinolone-3-carboxylate) and related compounds

Yoshihisa Kurasawa, Kiminari Yoshida, Naoki Yamazaki, Eisuke Kaji, Kenji Sasaki, Yoshito Zamami, Takatoshi Fujii, Min Zhao, Hideyuki Ito, Haruhiko Fukaya

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Abstract

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.

Original languageEnglish
Pages (from-to)1720-1726
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume51
Issue number6
DOIs
Publication statusPublished - Nov 2014

ASJC Scopus subject areas

  • Organic Chemistry

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