1-甲基-3-丙基-4-氨基吡唑-5-甲腈的研究

doi:10.6023/cjoc201512042

摘要/Abstract

以1-甲基-3-丙基吡唑-5-甲酸为原料，经酰化、脱水、硝化、还原反应合成了1-甲基-3-丙基-4-氨基吡唑-5-甲腈，然后与醛类缩合得到吡唑并嘧啶酮衍生物. 在Pd/C催化氢化1-甲基-3-丙基-4-硝基吡唑-5-甲腈的过程中，利用HPLC和HPLC-HRMS分离检测到硝基还原为氨基过程的3个中间体：羟胺、氧化偶氮、偶氮化合物，提出了可能的还原机理. 产物结构经¹H NMR，¹³C NMR，IR和MS分析表征.

关键词: 1-甲基-3-丙基-4-氨基吡唑-5-甲腈, 吡唑并嘧啶酮衍生物, 还原机理

1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile was synthesized by using 1-methyl-3-propylpyrazole-5-formic as starting materials in four steps reaction including acylation, dehydration, nitrification and reduction. Then pyrazolopyrimidinone derivatives were obtained from the condensation of 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile and aldehydes. 1-Methyl-3-propyl-4-nitropyrazole-5-carbonitrile was reduced to amine in the presence of palladium-charcoal. Three intermediate products, hydroxylamine, azoxypyrazole and azopyrazole, were separated and detected with HPLC and HPLC-HRMS during the formation of amine pyrazole. Possible reduction mechanism was proposed. The structures of products were characterized by ¹H NMR, ¹³C NMR, IR spectra and MS.

Key words: 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile, pyrazolopyrimidinone derivative, reduction mechanism

引用此文

徐敏, 史大昕, 刘明星, 张奇, 李加荣. 1-甲基-3-丙基-4-氨基吡唑-5-甲腈的研究[J]. 有机化学, 2016, 36(7): 1611-1616.

Xu Min, Shi Daxin, Liu Mingxing, Zhang Qi, Li Jiarong. Study of 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile[J]. Chin. J. Org. Chem., 2016, 36(7): 1611-1616.

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