title: Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds.
abstract: New routes to 2, 4, 5-trisubstituted oxazoles were established whereby the substitution pattern was established by the structure of the starting nonsymmetrical acyloins. 2-Chloromethyl-4, 5-disubstituted oxazoles were prepared by refinements of an earlier described process whereby chloroacetyl esters of symmetrical and non-symmetrical acyloins were cyclized using an ammonium acetate/acetic acid protocol. After substitution is effected, the azide moiety is then installed by substitution under mild conditions. While dibrominated and iodinated phenyloxazoles are required for further synthetic elaboration, the cyclization reaction was found to be very sensitive to the relative positions of the halogens in the starting materials.
authors.affiliation: Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, Kentucky, 40292, USA.
authors.forename: Pravin C
authors.initials: PC
authors.lastname: Patil
authors.affiliation: Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, Kentucky, 40292, USA.
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Luzzio
authors.affiliation: Department of Periodontics, Endodontics and Dental Hygiene, University of Louisville School of Dentistry, 501 S. Preston St. Louisville, Kentucky, 40292 USA.
authors.forename: Donald R
authors.initials: DR
authors.lastname: Demuth
keywords: Azides; Biofilms; Click Chemistry; Oxazoles; Peptidomimetics