Significant acceleration of 6π-azaelectrocyclization resulting from a remarkable substituent effect and formal synthesis of the ocular age pigment A2-E by a new method for substituted pyridine synthesis

被引：134

作者：

Tanaka, K ^{[1
]}

Mori, H ^{[1
]}

Yamamoto, M ^{[1
]}

Katsumura, S ^{[1
]}

机构：

[1] Kwansei Gakuin Univ, Sch Sci, Nishinomiya, Hyogo 6628501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 09期

关键词：

D O I：

10.1021/jo005779+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The remarkable acceleration of 6 pi -azaelectrocyclization due to the combination of the C4-carbonyl and the C6-alkenyl or phenyl substituents in 1-azatrienes was found. This observation was rationalized by considering the remarkable orbital interaction between the HOMO and LUMO of 1-azatrienes, which were obtained by molecular orbital calculations. The formal synthesis of the unusual retinal metabolite, A2-E, was achieved by two types of the new one-pot synthesis of substituted pyridines by utilizing the obtained facile 6 pi -azaelectrocyclization, one of which is compatible with the proposed metabolic pathway of A2-E.

引用

页码：3099 / 3110

页数：12

共 67 条

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