Synthesis and NMR spectroscopic investigations with 3-amino-, 3-hydroxy-, and 3-methoxy-4-acyl-1-phenyl-2-pyrazolin-5-ones

Synthesis and NMR spectroscopic investigations with 3-amino-, 3-hydroxy-, and 3-methoxy-4-acyl-1-phenyl-2-pyrazolin-5-ones
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DOI:
10.3987/com-04-10046
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发表时间:
2004-06-01
期刊:
影响因子:
0.6
通讯作者:
Hallak, L
Hallak, L
中科院分区:
化学4区
文献类型:
--
作者:
Holzer, W;Hallak, L

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在1,4-二氧六环中,3-氨基-、3-羟基-和3-甲氧基-1-苯基-2-吡唑啉-5-酮与羧酰氯/氢氧化钙反应,主要得到相应的4-酰基-2-吡唑啉-5-酮。3-甲氧基-1-苯基-2-吡唑啉-5-酮与二甲基甲酰胺二乙缩醛反应得到4-二甲氨基亚甲基产物的(E)/(Z)-混合物,与四氰基乙烯反应得到4-二氰基亚甲基产物,而与亚硝酸反应得到4-羟肟基衍生物。NMR-光谱研究(H-1,C-13,N-15)与所获得的反应产物。
Reaction of 3-amino-, 3-hydroxy- and 3-methoxy-1-phenyl-2-pyrazolin-5-one with carboxylic acid chlorides/calcium hydroxide in 1,4-dioxane mainly affords the corresponding 4-acyl-2-pyrazolin-5-ones. 3-Methoxy-1-phenyl-2-pyrazolin-5-one reacts with dimethylformamide diethyl acetal to give an (E)/(Z)-mixture of the 4-dimethylaminomethylene product, with tetracyanoethylene the 4-dicyanomethylene product is obtained, whereas with nitrous acid the 4-hydroximino derivative results. NMR-spectroscopic investigations (H-1, C-13, N-15) with the obtained reaction products are presented.