Document Type
Presentation - Oral - to academic peers, less than or equal to 1 hour
Novel Synthesis of Heterocyclics Containing a Benzoquinone or Benzoquinoneimine Ring
Department
Chemistry
Date of Activity
5-22-2017
Abstract
Benzoquinone and benzoquinoneimine rings were synthesized for two different projects. No good leaving groups were utilized to insert the alkylthio- or alkylamino groups into these heterocyclic rings. Quinoline-5,8-dione intermediate was synthesized from the oxidation of 5- or 8-quinolinol with [bis(trifluoroacetoxy)iodo]benzene, PIFA. A new variety of 6,7-bis(alkylthio- or alkylamino-substituted)quinoline-5,8-diones were prepared in one pot synthesis from the addition of alkylthiols or alkylamines to quinoline-5,8-dione after subsequent oxidation with NaIO4. These compounds will be further tested as anti-inflammatory, anti-bacterial, and or tuberculostatic inhibitors. A series of 2-thio-substituted-3H-phenothiazin-3-ones was effectively synthesized in one pot treatment of a 2-alkylthio-1,4-benzoquinone with 1,2-aminothiophenol followed by oxidation with NaIO4. These compounds will be assessed for their activity as psychopharmacological drugs and other disorders of the central nervous system (CNS) or as anti-infective pharmacophores (Figure1).
Recommended Citation
Novel Synthesis of Heterocyclics Containing a Benzoquinone or Benzoquinoneimine Ring. Author: Herman H. Odens. 100th Canadian Chemistry Conference and Exhibition, Toronto, Ontario, May 28 & June 1, 2017.