摘要
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,^(13)C NMR,IR和MS分析表征.
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 pyrazolopyrim- idinone 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 interme- diate 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 1^H NMR, 13^C NMR, IR spectra and MS.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2016年第7期1611-1616,共6页
Chinese Journal of Organic Chemistry
