Vilsmeier-Haak formylation of 3,5-dimethylpyrazoles
Vilsmeier-Haak formylation of 3,5-dimethylpyrazoles
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DOI：
10.1134/s1070363206110260
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发表时间：
2006-11-01
影响因子：
0.9
通讯作者：
Matsoyan, S. G.
中科院分区：
文献类型：
--
作者：
Attaryan, O. S.;Antanosyan, S. K.;Matsoyan, S. G.
根据Vilsmeier-Haak的N-烷基-3，5-二甲基-1H-吡唑的甲酰化导致形成相应的4-甲酰基衍生物。在类似条件下，氮原子上没有取代基的3，5-二甲基-1H-吡唑不能在4位进行取代。以[3-（4-甲酰基-3，5-二甲基-1H-吡唑-1-基）丙酸甲酯]为原料，经碱性水解后，加热生成酸，合成了3，5-二甲基-1H-吡唑-4-甲醛。
Formylation of N-alkyl-3,5-dimethyl-1H-pyrazoles according to Vilsmeier-Haak led to the formation of the corresponding 4-formyl derivatives. 3,5-Dimethyl-1H-pyrazole having no substituent on the nitrogen atom failed to undergo formylation at the 4 position under analogous conditions. 3,5-Dimethyl-1H-pyrazole-4-carbaldehyde was synthesized by alkaline hydrolysis of methyl [3-(4-formyl-3,5-dimethyl-1H-pyrazol-1-yl)propionate and subsequent heating of the acid thus formed.