Nitropyrazoles 16. The use of methoxymethyl group as a protecting group for the synthesis of 4-methyl-3-nitro-5-R-pyrazoles

被引：0
|
作者：
A. A. Zaitsev
I. O. Kortusov
I. L. Dalinger
V. V. Kachala
G. P. Popova
S. A. Shevelev
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
[2] D. I. Mendeleev University of Chemical Technology of Russia,undefined
来源：
Russian Chemical Bulletin | 2009年 / 58卷
关键词：
nitropyrazoles; dinitropyrazoles; nitration; nucleophilic substitution; nucleophiles; protecting groups;
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摘要：
4-Methyl-3,5-dinitropyrazole prepared by nitration of 1,4-dimethylpyrazole readily reacts with methoxymethyl chloride and methyl vinyl ketone in acetonitrile in the presence of a base giving 1-methoxymethyl-4-methyl-3,5-dinitropyrazole and 4-methyl-3,5-dinitro-1-(3-oxobutyl)pyrazole, respectively. The action of the thioglycolanilide anion on 4-methyl-3,5-dinitro-1-(3-oxobutyl)pyrazole results only in the removal of 1-protecting group and the formation of 2-[(3-oxobutyl)thio]acetanilide, while the action of anionic S-nucleophiles on 1-methoxymethyl-4-methyl-3,5-dinitropyrazole leads to the substitution products of the 5-NO2 group in which the methoxymethyl group can be removed by acid hydrolysis.
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页码：2118 / 2121
页数：3
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