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
收藏
页码：5965 / 5971
页数：7
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