Ring-fluorinated isoquinoline and quinoline synthesis:: Intramolecular cyclization of o-cyano- and o-isocyano-β,β-difluorostyrenes

被引：87

作者：

Ichikawa, J ^{[1
]}

Wada, Y

Miyazaki, H

Mori, T

Kuroki, H

机构：

[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[2] Kyushu Inst Technol, Dept Appl Chem, Kitakyushu, Fukuoka 8048550, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 09期

关键词：

D O I：

10.1021/ol034192p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic o-Cyano-beta,beta-difluorostyrenes react with organolithiums selectively at the cyano carbon to generate the corresponding sp(2) nitrogen anions, which in turn undergo intramolecular replacement of the vinylic fluorine to afford 3-fluoroisoquinolines. Similarly, the reaction of beta,beta-difluoro-o-isocyanostyrenes with organomagnesiums or -lithiums generates the corresponding sp(2) carbanions on the isocyano carbon. Subsequent cyclization via substitution of the fluorine leads to 3-fluoroquinolines.

引用

页码：1455 / 1458

页数：4

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