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


  •  Kevin Cannon    
  •  Deepa Gandla    
  •  Samantha Lauro    
  •  Lee Silverberg    
  •  John Tierney    
  •  Anthony Lagalante    

Abstract

1,3-thiazolidin-4-ones, also known as thiazolidin-4-ones, are known to have a very wide range of biological activity. The corresponding S-oxides may show enhanced activity, and therefore viable synthetic routes to these S-oxides are required. S-oxidation of 3-cyclohexyl-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 at high temperature by increasing the equivalents of Oxone® used; the extent of this selectivity was affected by the substituent of the aromatic ring. In those cases in which the reaction produced a mixture of the sulfoxide and sulfone, the ratio of the products was quantified by 1H NMR.



This work is licensed under a Creative Commons Attribution 4.0 License.
  • Issn(Print): 1916-9698
  • Issn(Onlne): 1916-9701
  • Started: 2009
  • Frequency: quarterly

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