Designing Synthetic Pathways for Several 2-Thio-Substituted-3H-Phenothiazin-3-ones in Preparation for Testing in Treatment of Central Nervous System Disorders

Authors

Preston H. Palm, Southern Adventist UniversityFollow
Herman H. Odens, Southern Adventist UniversityFollow

Document Type

Other

Publication Date

Winter 12-15-2015

Abstract

This paper investigates possible synthetic pathways for two 2-thio-substituted-3H-phenothiazin-3-ones (7). A two step reaction in which 1,4-benzoquinone (1) is first reacted with an alkylthiol (2) in the presence of sodium periodate (NaIO₄) and then treated with 2-aminothiophenol (5) followed by a second oxidation with sodium periodate was demonstrated to be effective in synthesizing 2-(phenylthio)-3H-phenothiazin-3-one (12). The same synthetic approach was shown to be ineffective in the synthesis of 2-(cyclopentylthio)-3H-phenothiazin-3-one (16) due to the fact that the first step was incapable of synthesizing 2-(cyclopentylthio)-1,4-benzoquinone (14). Several other synthetic routes were also proven to be ineffective. This investigation is part of a larger effort to create a vast library of 2-thio-substituted-3H-phenothiazin-3-ones (7) for testing in leukotriene inhibition and treatment of neurodegenerative disorders.

Recommended Citation

Palm, Preston H. and Odens, Herman H., "Designing Synthetic Pathways for Several 2-Thio-Substituted-3H-Phenothiazin-3-ones in Preparation for Testing in Treatment of Central Nervous System Disorders" (2015). Capstone Research Projects. 184.
https://knowledge.e.southern.edu/senior_research/184