Novel one-pot synthesis of 2-thio-substituted-3-H-phenothiazin-3-ones driven by oxidation with sodium periodate

Autor: Herman H Odens Jr., Jae Y You, Alexandria D Gallimore, Preston H Palm, Cameron W Davis, Josue M Bahena, Jeffrey S Moser, Mackenzie E Smith, Herman H Odens
Rok vydání: 2022
DOI: 10.3762/bxiv.2022.36.v1
Popis: A series of novel 2-thio-substituted-3H-phenothiazin-3-ones (6h-l) was effectively synthesized in one pot after optimization of the four-step synthesis. Treatment of a 2-alkylthio-1,4-benzoquinone (3a-l) made in situ and condensed with 1,2-aminothiophenol (5) followed by oxidation with NaIO4 produced the desired final targets. A four-step reaction sequence in which 1,4-benzoquinone (1) is first reacted with an alkylthiol (2a-l) 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-thio-substituted-3H-phenothiazin-3-ones (6a-g). The one-pot synthesis is an improvement of the stepwise synthesis of these 2-thio-substituted-3H-phenothiazin-3-one heterocycles since four steps are run in sequence and treated as one.
Databáze: OpenAIRE