Conversion of N-acyl-4-acyloxy-β-lactams into 1,3-oxazin-6-ones:: Two consecutive pseudopericyclic processes
Conversion of N-acyl-4-acyloxy-β-lactams into 1,3-oxazin-6-ones:: Two consecutive pseudopericyclic processes
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DOI：
10.1021/ol0056168
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发表时间：
2000-04-06
期刊：
影响因子：
5.2
通讯作者：
Ochoa, G
中科院分区：
文献类型：
--
作者：
Alajarín, M;Vidal, A;Ochoa, G
[图形]n-酰基-4-酰基氧基- β -内酰胺在碱性条件下转化为1,3-恶嗪-6- 1。这种转化被认为是通过n -酰基酮进行的，n -酰基酮通过两个电环过程的序列重新排列成最终产物。计算得到的两种协同反应的（RHF和B3LYP）跃迁结构显示出特征的伪环轨道拓扑结构。
[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.