An improved procedure for the regiospecific synthesis of electron deficient 4- and 6-substituted isatins.

被引：29

作者：

Kraynack, EA ^{[1
]}

Dalgard, JE ^{[1
]}

Gaeta, FCA ^{[1
]}

机构：

[1] Geron Corp, Dept Chem, Menlo Park, CA 94025 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 42期

关键词：

annulation; nitrogen heterocycles; nitro compounds; regiospecificity;

D O I：

10.1016/S0040-4039(98)01719-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiospecific synthesis of 4- and 6-substituted isatins 5a-g in four steps from halonitrobenzenes 1a-g has been investigated for a variety of substrates (Scheme 1). The procedure makes use of readily available, easily handled materials and in most cases purification of neither intermediates nor final products is required. Yields of isatins are between 26 and 75% (Table 1). Improved yields of known isatins are reported as well as the syntheses of previously unreported isatins. This method, taken together with known procedures, provides for the synthesis of the full complement of isatin regioisomers. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7679 / 7682

页数：4

共 14 条

[1] 4-substituted-3-phenylquinolin-2(1H)-ones: Acidic and nonacidic glycine site N-methyl-D-aspartate antagonists with in vivo activity [J].