title: Synthesis of Extended Oxazoles III: Reactions of 2-(Phenylsulfonyl)methyl-4,5-diaryloxazoles.
abstract: 2-((Phenylsulfonyl)methyl)-4,5-diphenyloxazole is a useful scaffold for synthetic elaboration at the 2-methylene position thereby affording extended oxazoles. The corresponding α-sulfonyl anion reacts smoothly with diverse alkyl halides giving monoalkylated (47-90%), dialkylated (50-97%), and cyclic (59-93%) products. The reductive desulfonylation of the monoalkylated and selected dialkylated products was optimized with a magnesium/mercuric chloride reagent system and afforded desulfonylated products in the range of 66-97%. The anti-inflammatory Oxaprozin was prepared using the α-sulfonyl carbanion strategy along with optimized desulfonylation.
authors.affiliation: Department of Chemistry, University of Louisville , 2320 South Brook Street, Louisville, Kentucky 40292, United States.
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, United States.
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Luzzio
mesh_terms: D000478:Alkylation; D015636:Magnesium Chloride / Q000737:chemistry; D008627:Mercuric Chloride / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013057:Spectrum Analysis / Q000379:methods*
chemical_list: D010080:Oxazoles; D015636:Magnesium Chloride; D008627:Mercuric Chloride