Novel Synthesis of 6,7-bis(alkylthio- or alkylamino-substituted)quinoline-5,8-dione via Nucleophilic Addition/Oxidation of Alkylthio and Alkylamino Derivatives to Quinoline-5,8-dione
Presenter Status
Undergraduate Student
Session
F-1
Location
CSH Room 108
Start Date
9-5-2014 2:00 PM
End Date
9-5-2014 2:30 PM
Presentation Abstract
A new variety of 6,7-bis (alkylthio- or alkylamino-substituted) quinoline-5,8-diones were prepared from the addition of mercaptans or amino nucleophiles to quinoline-5,8-dione after subsequent oxidation with NaIO4. Mono addition of the nucleophiles to the quinoid ring was observed for the case when the first nucleophilic addition would produce steric hindrance for a second nucleophilic attack. The core quinoline-5,8-dione intermediate was prepared from the oxidation of 5-quinolinol or 8-quinolinol with [bis(trifluoroacetoxy)iodo] benzene, PIFA, in the presence of water and acetonitrile as solvents. No good leaving groups were utilized to insert the alkylthio or alkylamino groups into the quinoline ring. The synthesized compounds will be tested for their anti-inflammatory, anti-bacterial and tuberculostatic inhibition activities.
Novel Synthesis of 6,7-bis(alkylthio- or alkylamino-substituted)quinoline-5,8-dione via Nucleophilic Addition/Oxidation of Alkylthio and Alkylamino Derivatives to Quinoline-5,8-dione
CSH Room 108
A new variety of 6,7-bis (alkylthio- or alkylamino-substituted) quinoline-5,8-diones were prepared from the addition of mercaptans or amino nucleophiles to quinoline-5,8-dione after subsequent oxidation with NaIO4. Mono addition of the nucleophiles to the quinoid ring was observed for the case when the first nucleophilic addition would produce steric hindrance for a second nucleophilic attack. The core quinoline-5,8-dione intermediate was prepared from the oxidation of 5-quinolinol or 8-quinolinol with [bis(trifluoroacetoxy)iodo] benzene, PIFA, in the presence of water and acetonitrile as solvents. No good leaving groups were utilized to insert the alkylthio or alkylamino groups into the quinoline ring. The synthesized compounds will be tested for their anti-inflammatory, anti-bacterial and tuberculostatic inhibition activities.