Ipso substitution as a route to benzo[c]quinolizines and 4-hydroxycoumarins

被引：6

作者：

Liu, Y ^{[1
]}

Kurth, MJ ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 07期

关键词：

D O I：

10.1021/jo0161126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient ipso substitution method for the preparation of benzo[c]quinolizine (2) and 4-hydroxy-3-(2'-pyridyl)coumarin (3) has been developed. The intramolecular nucleophilic substitution reaction of 3-oxo-2-(2'-pyridyl)-(2-halophenyl)propanoate (1) in refluxing xylenes gives initially benzo[c]quinolizine, while further heating results in the formation of 4-hydroxycoumarin. A mechanism has been proposed to rationalize the two competitive reaction pathways, and the role of HCl is discussed. Under optimized conditions, seven benzo(c]quinolizines and five coumarins were prepared in moderate to good yields.

引用

页码：2082 / 2086

页数：5

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