Copper catalyzed access to functionalized oxazoles from oximes via carbenoids |
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Authors: | Anugula Nagaraju K Sandeep KC Kumara Swamy |
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Institution: | School of Chemistry, University of Hyderabad, Hyderabad 500046, India |
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Abstract: | An operationally simple, economical and straightforward synthesis of diverse oxazoles from oximes possessing a vicinal carbonyl group has been achieved by treatment of the latter with terminal diazo compounds like ethyl/benzyl diazoacetate and diazoacetophenone (which act as carbenoids) in one pot. At least two reducible functional groups (two ester groups or cyano?+?ester) are simultaneously introduced in one step. This reaction involves expulsion of a molecule each of N2 and water only as byproducts under copper catalysis. The structure of one of these oxazoles is confirmed by X-ray crystallography. Both the ester groups in the oxazole product could be reduced to alcohol moieties by using NaBH4/EtOH. |
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Keywords: | Oxazole Oxime Diazo acetate Carbenoid Copper catalyzed |
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