Nov, 2014
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
- ,
- ,
- ,
- ,
- ,
- ,
- ,
- ,
- ,
- Volume
- 51
- Number
- 6
- First page
- 1720
- Last page
- 1726
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1002/jhet.1861
- Publisher
- 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.
- Link information
-
- DOI
- https://doi.org/10.1002/jhet.1861
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000345457700021&DestApp=WOS_CPL
- URL
- http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84915789069&origin=inward
- ID information
-
- DOI : 10.1002/jhet.1861
- ISSN : 0022-152X
- eISSN : 1943-5193
- SCOPUS ID : 84915789069
- Web of Science ID : WOS:000345457700021