Expedient Synthesis of 1-Hydroxy-4- and 1-Hydroxy-6-nitroindoles

被引：19

作者：

Bujok, Robert ^{[1
]}

Wrobel, Zbigniew ^{[1
]}

Wojciechowski, Krzysztof ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland

来源：

SYNLETT | 2012年 / 09期

关键词：

indoles; acylation; reduction; nucleophilic aromatic substitution; tin; ketones; NUCLEOPHILIC-SUBSTITUTION; N-HYDROXYINDOLES; ISOFORM; 5; CHEMISTRY; DERIVATIVES; INDOLES; HYDROGEN; 1-HYDROXYTRYPTOPHANS; 1-METHOXYINDOLES; INHIBITORS;

D O I：

10.1055/s-0031-1291044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of alpha-chloroalkyl ketones with 1,3-dinitrobenzenes provides 2,4-dinitrobenzyl ketones which when reduced with tin(II) chloride form 6-nitro derivatives of 1-hydroxyindoles. An alternative approach is the condensation of 2,4- and 2,6-dinitrotoluenes with diethyl oxalate or ethyl trifluoroacetate provides dinitrobenzyl ketones which leads after reduction with tin(II) chloride to nitro derivatives of 1-hydroxyindol-2-carboxylates or 1-hydroxy-2-(trifluoromethyl)indoles, respectively.

引用

页码：1315 / 1320

页数：6

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