Incorporation of heterocyclic moieties, such as an oxazole, can improved solubility, rigidity, and ability to accept hydrogen-bonds.  Recently, our group showed the synthesis of oxazoles through a two-step procedure starting from an explode.  First, an epoxide was opened in the presence of a Lewis acid to form a b-amino alcohol.  This was followed by an oxidation using manganese dioxide.  This method tolerates a variety of epoxide substrates, as well as a wide range of substituents at the 2-position of the oxazole.  When other oxidizing agents were explored, such as <i>N</i>-bromosuccinimide (NBS) or 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), we were able to chemoselectively oxidize the b-amino alcohol to oxazoline and 4-bromooxazoline, respectively.  Structrally rigid compounds such as 1,10-phenanthroline offers insight into the oxidation mechanism.  When NBS and DBDMH were used to oxidize 1,10-phenanthrolineaminoalcohol, only oxazoles were were isolated.  <br/>

Synthesis and characterization of functionalized heterocyclic compounds: 1,10-phenanthrolines and oxazoles

254th National Meeting (2017)

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