title: Synthesis of extended oxazoles II: Reaction manifold of 2-(halomethyl)-4,5-diaryloxazoles.
abstract: 2-(Halomethyl)-4,5-diphenyloxazoles are effective, reactive scaffolds which can be utilized for synthetic elaboration at the 2-position. Through substitution reactions, the chloromethyl analogue is used to prepare a number of 2-alkylamino-, 2-alkylthio- and 2-alkoxy-(methyl) oxazoles. The 2-bromomethyl analogue offers a more reactive alternative to the chloromethyl compounds and is useful in the C-alkylation of a stabilized (malonate) carbanion as exemplified by a concise synthesis of Oxaprozin.
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
keywords: Oxaprozin; click chemistry; heterocycles; ligands; oxazoles