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Spectroscopic Properties of Oxazoles
Oxazole DielsAlder Reactions
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1,3-dipolar cycloaddition 1,3-DIPOLAR CYCLOADDITION REACTIONS 2,5-disubstituted Abstr Ac2O acetic acid methyl ester acylation adduct afforded aldehyde alkyl amide analogs anhydride authors benzene bis-oxazole BOCHN Burgess reagent calyculin CDCl3 CH3 CH3 CH3 CH3 H CH3CN CH3O CH3OH Chem chemistry chloride co-workers CO2Et CO2H compounds converted COOC2H5 COOCH3 COOH coupling cyclization cyclodehydration Data from ref diastereomers Diels-Alder reaction dienophile DMAD ester excellent yield Figure fragment furan gave H CH3 Heterocycl hydrolysis Ibata intermediate intramolecular isolated isomunchnone ketone Lewis acid methodology methyl mixture n-Buli natural products nitrile nucleophilic OCH3 overall yield oxazole oxazole ring oxazoline oxidation Padwa Perkin Trans Ph H Ph Ph prepared pyridine pyrroles reacted reaction conditions rearrangement reflux regioselective ring opening shown in Table steps substituted synthesis synthetic Tetrahedron Lett toluene yield Scheme