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Synthesis of 3- tert -Butyl-4-hydroxy-1,4-dihydropyrazolo[5,1- c ][1,2,4]triazines
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-05-26 , DOI: 10.1134/s1070428020040065
L. M. Mironovich , S. M. Ivanov , N. G. Kolotyrkina

Abstract

Two new approaches have been proposed for the synthesis of 4-hydroxy-1,4-dihydropyrazolo[5,1-c]-[1,2,4]triazines via (1) borohydride reduction of 1-R-4-oxo-1,4-dihydro derivatives and (2) Vilsmeier formylation of 3-tert-butyl-8-methylpyrazolo[5,1-c][1,2,4]triazine. 3-tert-Butylpyrazolo[5,1-c][1,2,4]triazin-1(5)-ium cation has been generated for the first time by treatment of 7-amino-1-benzyl-3-tert-butyl-4-hydroxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carbonitrile with trifluoroacetic acid in CDCl3. The hydrolysis of 4-alkoxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines was monitored by 1H and 13C NMR spectroscopy. The structure of the synthesized compounds was confirmed by spectral and X-ray diffraction data.


中文翻译:

3-叔丁基-4-羟基-1,4-二氢吡唑并[5,1-c] [1,2,4]三嗪的合成

摘要

已提出了两种新方法,用于通过(1)硼氢化物还原1-R-4-氧代-(4-)-1,4-二氢吡唑并[5,1- c ]-[1,2,4]三嗪1,4-二氢衍生物和(2)3-丁基-8-甲基吡唑并[5,1- c ] [1,2,4]三嗪的Vilsmeier甲酰化。3--Butylpyrazolo [5,1- c ^ ] [1,2,4]三嗪-1(5)阳离子鎓已通过治疗的7-氨基-1-苄基-3-首次生成的-丁基-4-羟基-1,4-二氢吡唑并[5,1- c ] [1,2,4]三嗪-8-腈与三氟乙酸的CDCl 3溶液。用1监测4-烷氧基-1,4-二氢吡唑并[5,1- c ] [1,2,4]三嗪的水解。1 H和13 C NMR光谱。合成的化合物的结构通过光谱和X射线衍射数据证实。
更新日期:2020-05-26
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