Conversion of N-acyl-4-acyloxy-β-lactams into 1,3-oxazin-6-ones:: Two consecutive pseudopericyclic processes

被引：45

作者：

Alajarín, M ^{[1
]}

Vidal, A ^{[1
]}

Sánchez-Andrada, P ^{[1
]}

Tovar, F ^{[1
]}

Ochoa, G ^{[1
]}

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 07期

关键词：

D O I：

10.1021/ol0056168

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] N-Acyl-4-acyloxy-beta-lactams are converted into 1,3-oxazin-6-ones under basic conditions. This transformation is believed to proceed via N-acylazetones, which rearrange to the final products by a sequence of two electrocyclic processes. The calculated (RHF and B3LYP) transition structures of both concerted reactions are shown to present characteristic pseudopericyclic orbital topologies.

引用

页码：965 / 968

页数：4

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