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

Submitting author affiliation:
University of Tennessee at Chattanooga, Chattanooga, TN, United States

Beilstein Arch. 2022, 202236. https://doi.org/10.3762/bxiv.2022.36.v1

Published 13 May 2022

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Abstract

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.

Keywords: 2-thio-substituted-3H-phenothiazin-3-ones, 2-alkylthio-1,4-benzoquinone, one-pot synthesis, addition/oxidation, heterocycles, psychopharmacological drugs, anti-infective pharmacophores

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Odens Jr., H. H.; You, J. Y.; Gallimore, A. D.; Palm, P. H.; Davis, C. W.; Bahena, J. M.; Moser, J. S.; Smith, M. E.; Odens, H. H. Beilstein Arch. 2022, 202236. doi:10.3762/bxiv.2022.36.v1

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