Selective Synthesis of Substituted 3-Aryl-2-phenyl-1,3-thiazolidin-4-one, Sulfoxides and Sulfones by S-Oxidation with Oxone

S-oxidation of 3-aryl-2-phenyl-1,3-thiazolidin-4-ones with Oxone® was investigated. For all compounds evaluated, selective oxidation to the sulfoxide was realized using 3 equivalents of Oxone® at room temperature. Alternatively, the sulfone was prepared selectively in most of the compounds evaluated at high temperature by increasing the equivalents of Oxone® used; the extent of this selectivity was affected by the substituent and its position on the N3 aromatic ring. The ratio of the sulfoxide and sulfone products was quantified by isolating the products by liquid chromatography.

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Work Title Selective Synthesis of Substituted 3-Aryl-2-phenyl-1,3-thiazolidin-4-one, Sulfoxides and Sulfones by S-Oxidation with Oxone
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Open Access
Creators
  1. Pepper, Matthew
  2. Selinsky, Rachel
  3. Lagalante, Anthony
  4. Cannon, Kevin
  5. Toovy, John
  6. Costa, Miguel Prates
Keyword
  1. thiazolidin-4-ones, oxone, sulfoxide, sulfone
License Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
Work Type Article
Publication Date July 12, 2017
Subject
  1. thiazolidin-4-ones, oxone, sulfoxide, sulfone
Publisher Identifier (DOI)
  1. https://doi.org/10.5539/ijc.v9n4p1
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Source
  1. International Journal of Chemistry
Deposited August 29, 2017

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Version 1
published

  • Created
  • Added 69056-253169-1-PB.pdf
  • Added Creator Pepper, Matthew
  • Added Creator Selinsky, Rachel
  • Added Creator Lagalante, Anthony
  • Added Creator Cannon, Kevin
  • Added Creator Toovy, John
  • Added Creator Costa, Miguel Prates
  • Published