Regiospecific synthesis of novel 6-amino-5-hydroxypyridazin-3(2H)-ones

被引：2

作者：

Dragovich, Peter S. ^{[1
]}

Blazel, Julie K. ^{[1
]}

Dao, Kimkim ^{[1
]}

Ellis, David A. ^{[1
]}

Li, Lian-Sheng ^{[1
]}

Murphy, Douglas E. ^{[1
]}

Ruebsam, Frank ^{[1
]}

Tran, Chinh V. ^{[1
]}

Zhou, Yuefen ^{[1
]}

机构：

[1] Anadys Pharmaceut, San Diego, CA 92121 USA

来源：

SYNTHESIS-STUTTGART | 2008年 / 04期

关键词：

pyridazin-3(2H)-ones; Dieckmann cyclization; hydrazones; amino- and chloro(hydrazono)acetates; heterocycles;

D O I：

10.1055/s-2008-1032157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a novel class of 6-amino-5-hydroxypyridazin-3(2H)-ones (3-oxo-2,3-dihydropyridazines) is described. These compounds also contain an ethoxycarbonyl moiety at the 4-position of the pyridazinone ring. They are prepared in good to moderate yields (30-72%) by the condensation of disubstituted amines with (alkythydrazono)- or (arylhydrazono)(chloro)acetates followed by subsequent acylation with ethyl malonyl chloride and Dieckmann cyclization. An initial assessment of the scope and limitations of the new methodology is described along with the novel synthesis of several (alkylhydrazono)(chloro)acetate substrates utilized in the pyridazinone preparations.

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收藏

页码：610 / 616

页数：7

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