Synthesis of [2-(Trimethylsilyl)ethynyl]pyrazoles Based on Bis(trimethylsilyl)acetylene and Arylacetyl Chlorides

被引：14

作者：

Pankova, Alena S. ^{[1
]}

Golubev, Pavel R. ^{[1
]}

Ananyev, Ivan V. ^{[2
]}

Kuznetsov, Mikhail A. ^{[1
]}

机构：

[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 30期

关键词：

Synthetic methods; Nitrogen heterocycles; Chemoselectivity; SUBSTITUTED PYRAZOLES; DERIVATIVES; COMPLEXES; ACID;

D O I：

10.1002/ejoc.201200807

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical approach to the synthesis of [2-(trimethylsilyl)ethynyl]pyrazoles was developed through condensation of hydrazines with enynones that are easily accessible frombis(trimethylsilyl)acetylene and arylacetyl chlorides. Optimized conditions for reactions with monoarylhydrazines permit the chemoselective formation of 5-alkynylpyrazoles in high yields (4894?%). When monoalkylhydrazines or the parent hydrazine is used, mixtures of 3- and 5-alkynylpyrazoles are formed in 7379?% yields. The method uses inexpensive starting materials and can be applied to a variety of substrates, which makes it convenient for the synthesis of alkynylpyrazoles.

引用

页码：5965 / 5971

页数：7

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