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有机化学 ›› 2004, Vol. 24 ›› Issue (9): 1045-1051. 上一篇    下一篇

研究论文

2'-芳基-3-(1,4,5,6-四氢-6-哒嗪酮-3-羰基)氨基硫脲及其环化产物的合成

王多志a, 曹玲华*,a,b   

  1. a新疆大学化学化工学院 乌鲁木齐 830046;
    b南开大学元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2004-01-05 修回日期:2004-03-15 接受日期:2004-03-15 发布日期:2022-09-20
  • 基金资助:
    国家自然科学基金(No. 29962002)资助项目.

Synthesis of 2'-Aryl-3-(1,4,5,6-tetrehydropyridazin-6-one-3-carbonyl)- thiosemicarbazide and Their Related Heterocyclic Compounds

WANG Duo-Zhia, CAO Ling-Hua*,a,b   

  1. aCollege of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046;
    bState Key Laboratory of Elemento-Organic Chemistry, Nankai University,Tianjin 300071
  • Received:2004-01-05 Revised:2004-03-15 Accepted:2004-03-15 Published:2022-09-20
  • Contact: * E-mail: clhxj@xju.edu.cn

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以α-酮戊二酸为起始原料,合成了1,4,5,6-四氢-6-哒嗪酮-3-甲酰肼(2),然后将2与异硫氰酸芳基酯反应得到相应的芳基氨基硫脲衍生物3a～3f. 用硫酸、醋酸汞或氢氧化钠分别将芳基氨基硫脲环化得到一系列新的1,3,4-噻二唑、1,3,4-噁二唑和1,2,4-三唑的衍生物.化合物的结构经元素分析,IR, 1H NMR和MS谱得以证实.

关键词: 哒嗪酮, 1,3,4-噻二唑, 1,3,4-噁二唑, 1,2,4-三唑-5-硫酮

1,4,5,6-Tetrahydro-3-hydrozinocarbonyl-6-pyridazinone (2) was synthesized from α-ketoglutaric acid and hydrazine hydrate. 2'-Aryl-3-(1,4,5,6-tetrahydropyridazin-6-one-3-carbonyl)thiosemicarbazides (3a～3f) were prepared bythe reaction of aryl isothiocyanates with compound 2. While compounds3a～3f cyclized under sulphuric acid, mercuric acetate or sodium hydroxide to afford the terminal heterocyclic compounds 1,3,4-thiadiazole, 1,3,4-oxadiazole or 1,2,4-triazol-5-thione derivatives. The structures were determined by IR, 1H NMR, MS and elemental analyses.

Key words: pyridazin-6-one, 1,3,4-thiadiazole, 1,3,4-oxadiazole, 1,2,4-triazol-5-thione