New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their o-methyloximes with hydrazine

被引：95

作者：

Lukin, Kirill ^{[1
]}

Hsu, Margaret C. ^{[1
]}

Fernando, Dilinie ^{[1
]}

Leanna, M. Robert ^{[1
]}

机构：

[1] Abbott Labs, GPRD Proc Res & Dev, N Chicago, IL 60064 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 21期

关键词：

EFFICIENT SYNTHESIS; INHIBITORS; HETEROCYCLES; POTENT; DERIVATIVES; SYNTHASE;

D O I：

10.1021/jo0613784

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.

引用

页码：8166 / 8172

页数：7

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