Synthetic routes to quinoline derivatives: Novel syntheses of 3-butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline

被引：24

作者：

Atkins, RJ ^{[1
]}

Breen, GF

Crawford, LP

Grinter, TJ

Harris, MA

Hayes, JF

Moores, CJ

Saunders, RN

Share, AC

Walsgrove, TC

Wicks, I

机构：

[1] SmithKline Beecham Pharmaceut, Dept Synthet Chem, Tonbridge TN11 9AN, Kent, England

[2] SmithKline Beecham Pharmaceut, Dept Med Chem, Harlow CM19 5AD, Essex, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 1997年 / 1卷 / 03期

关键词：

D O I：

10.1021/op9700035

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The 3,4,8-trisubstituted quinoline derivatives 2-butyryl-8-methoxy-4-[(2-methylphenyl)amino] quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino] were prepared using five novel synthetic strategies, each involving a different disconnection as a basis for the key step. One such strategy led to the development of highly efficient processes for the large-scale preparations of both compounds and featured a facile cyclisation of an [(arylamino)methylene]malonate and an unusual Reformatsky reaction of a quinoline-3-carboxylate with tert-butyl 2-bromobutyrate in the presence of zinc.

引用

页码：185 / 197

页数：13

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