Abstract
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.
Highlights
S-oxidation of 3-aryl-2-phenyl-1,3-thiazolidin-4-ones with Oxone® was investigated
We have previously reported the reaction of ortho-substituted 2-aryl-3-cyclohexyl-1,3-thiazolidin-4-ones with Oxone®.(Cannon et al, 2015) For all ten compounds previously evaluated, selective oxidation to the sulfoxide was realized using 3 equivalents of Oxone® at room temperature, and subsequent oxidation to the sulfone was not observed under these reaction conditions after 25 hours
We report the high temperature oxidation of a series of meta- and para-substituted 3-aryl-2-phenyl-1,3-thiazolidin-4-ones with Oxone® to determine if 1) substituents on the N3 aromatic ring affect oxidative selectivity and 2) compare the substituent effects on the N3 aromatic ring to those previously reported on the C2 aromatic ring
Summary
1,3-Thiazolidin-4-ones, known as thiazolidin-4-ones, are known to have a very wide range of biological activity. (Suryawanshi et al, 2017) (Kaushal & Kaur, 2016) (Kumar, Kumar, Mundlia, Pradhan & Malik, 2015) (Tripathi et al, 2014) (Jain, Vaidya, Ravichandran, Kashaw, & Agrawal, 2012) (Abhinit, Ghodke & Pratima, 2009) (Hamama, Ismail, Shaaban & Zoorob, 2008) (Singh, Parmar, Raman, Virgil & Stenberg, 1981) (Brown, 1961), so much that some have referred to it as a “magic moiety” or “wonder nucleus”(Jain et al, 2012). There are ample examples of Oxone®-based oxidations of sulfides, there is little data related to the oxidation of thiazolidin-4-ones. We have previously reported the reaction of ortho-substituted 2-aryl-3-cyclohexyl-1,3-thiazolidin-4-ones with Oxone®.(Cannon et al, 2015) For all ten compounds previously evaluated, selective oxidation to the sulfoxide was realized using 3 equivalents of Oxone® at room temperature, and subsequent oxidation to the sulfone was not observed under these reaction conditions after 25 hours. We report the high temperature oxidation of a series of meta- and para-substituted 3-aryl-2-phenyl-1,3-thiazolidin-4-ones with Oxone® to determine if 1) substituents on the N3 aromatic ring affect oxidative selectivity and 2) compare the substituent effects on the N3 aromatic ring to those previously reported on the C2 aromatic ring. We report room temperature oxidations of this series of thiazolidin-4-ones with Oxone® and KMnO4 to ascertain the scope and selectivity of the Oxone® oxidations
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