Acylation of heterocyclic ketene aminals with propionyl chloride

被引:11
|
作者
Huang, ZT
Wang, JC
Wang, LB
机构
[1] Institute of Chemistry, Academia Sinica
关键词
D O I
10.1080/00397919608004539
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heterocyclic ketene aminals 1 or 2 reacted with propionyl chloride to give both the mono-N- and C-acylated products 4 and 5 or 6 and 7. While N-methyl heterocyclic ketene aminals 3 reacted with propionyl chloride under the same condition, the reaction took place in complexity. Besides N- and C-acylation, the O-attack and heterocyclic ring cleavage also occurred to give products 8 and 9.
引用
收藏
页码:2285 / 2295
页数:11
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