REACTION OF OXIMES WITH DIMETHYL CARBONATE - A NEW ENTRY TO 3-METHYL-4,5-DISUBSTITUTED-4-OXAZOLIN-2-ONES

被引：39

作者：

MARQUES, CA

SELVA, M

TUNDO, P

MONTANARI, F

机构：

[1] UNIV VENEZIA, DIPARTIMENTO SCI AMBIENTALI, CALLE LARGA S MARTA 2137, I-30123 VENICE, ITALY

[2] UNIV MILAN, DIPARTIMENTO CHIM ORGAN & IND, I-20133 MILAN, ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 21期

关键词：

D O I：

10.1021/jo00073a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190-degrees-C and in the presence of K2CO3 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 C=N bond. Nonoptimized yields range from 22 to 48%. The reaction seems to be a [3,3] sigmatropic rearrangement where DMC plays a key role in causing the initial N-methylation of the oximes.

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页码：5765 / 5770

页数：6

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