Reaction of oximes with dimethyl carbonate: a new entry to 3-methyl-4, 5-disubstituted-4-oxazolin-2-ones

CA Marques, M Selva, P Tundo…

文献索引：Marques, C. A.; Selva, M.; Tundo, P.; Montanari, F. Journal of Organic Chemistry, 1993 , vol. 58, # 21 p. 5765 - 5770

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被引用次数: 44

摘要

The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190" C and in the presence of KzCO3 yields 3-methyl-4, 5-disubstituted-4-oxazolin-2- ones. The reaction can be applied to both aliphatic and aromatic ketone oximes, provided that a methylene group be present near the CN bond. Nonoptimized yields range from 22 to 48%. The reaction seems to be a [3, 3] sigmatropic rearrangement where DMC plays a ...