N-allyl-2-(quinoline-2-carbonyl)hydrazinecarbothioamide | 1125771-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-allyl-2-(quinoline-2-carbonyl)hydrazinecarbothioamide
• 英文别名: 1-Prop-2-enyl-3-(quinoline-2-carbonylamino)thiourea
• CAS: 1125771-71-2
• 化学式: C₁₄H₁₄N₄OS
• 分子量: 286.357
• InChiKey: KRGCPNONTOGYRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-allyl-2-(quinoline-2-carbonyl)hydrazinecarbothioamide 在 三氯氧磷 作用下， 反应 4.0h， 以66%的产率得到N-prop-2-enyl-5-quinolin-2-yl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis and Reactions of Some New Quinoline Thiosemicarbazide Derivatives of Potential Biological Activity

  摘要：

  Quinoline-2-carbohydrazide (3) was reacted with aryl or alkyl isothiocyanates to give the corresponding quinoline thiosemicarbazides (4a-e). Cyclization of the substituted thiosemicarbazides with sodium hydroxide led to the formation of 5-(quinolin-2-yl)-2H-1, 2, 4-triazole-3(4H)-thiones (5a-e). Desulfurization of thiosemicarbazides by mercuric oxide gave 5-(quinolin-2-yl)-1, 3, 4-oxadiazol- 2-amines (6a-e). Treatment of thiosemicarbazides with ethyl bromoacetate or -bromopropionic acid yielded (Z)-N'-(3-substituted thiazolidin-4-oxo-2-ylidene) quinoline-2-carbohydrazides (7a-d), (8a-d), respectively. Treatment of thiosemicarbazides with chloroacetone furnished (Z)-N'-(4-methyl-3-substituted-thiazol-2(3H)-ylidene) quinoline-2-carbohydrazides (9a-d). Furthermore, the reaction of thiosemicarbazides with phosphorus oxychloride gave N-substituted-5-(quinolin-2-yl)-1,3,4-thiadiazol-2-amines (10a-e). All newly synthesized compounds were tested and evaluated for antimicrobial activity.

  DOI：

  10.1080/10426500701641304
• 作为产物：
  描述：

  喹啉-2-甲酰肼 、 天然芥菜籽油 以 1,4-二氧六环 为溶剂， 以85%的产率得到N-allyl-2-(quinoline-2-carbonyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and Reactions of Some New Quinoline Thiosemicarbazide Derivatives of Potential Biological Activity

  摘要：

  Quinoline-2-carbohydrazide (3) was reacted with aryl or alkyl isothiocyanates to give the corresponding quinoline thiosemicarbazides (4a-e). Cyclization of the substituted thiosemicarbazides with sodium hydroxide led to the formation of 5-(quinolin-2-yl)-2H-1, 2, 4-triazole-3(4H)-thiones (5a-e). Desulfurization of thiosemicarbazides by mercuric oxide gave 5-(quinolin-2-yl)-1, 3, 4-oxadiazol- 2-amines (6a-e). Treatment of thiosemicarbazides with ethyl bromoacetate or -bromopropionic acid yielded (Z)-N'-(3-substituted thiazolidin-4-oxo-2-ylidene) quinoline-2-carbohydrazides (7a-d), (8a-d), respectively. Treatment of thiosemicarbazides with chloroacetone furnished (Z)-N'-(4-methyl-3-substituted-thiazol-2(3H)-ylidene) quinoline-2-carbohydrazides (9a-d). Furthermore, the reaction of thiosemicarbazides with phosphorus oxychloride gave N-substituted-5-(quinolin-2-yl)-1,3,4-thiadiazol-2-amines (10a-e). All newly synthesized compounds were tested and evaluated for antimicrobial activity.

  DOI：

  10.1080/10426500701641304

文献信息

• Synthesis and Tuberculostatic Activity of Novel 1,2,4-Triazoles Obtained from Heterocyclic Carbohydrazides
  作者：Katarzyna Gobis、Henryk Foks、Zofia Zwolska、Ewa Augustynowicz-Kopeć

  DOI：10.3987/com-09-11888

  日期：——

  The novel 1,2,4-triazole derivatives have been synthesized by a few different pathways. Heterocyclic carbohydrazides were used to obtain monoesters of hydrazine acids (1-6), thiosemicarbazide derivatives (7-17), and finaly 1,2,4-triazole-5-thiones (18-38). Carbohydrazides were also cyclized with methyl carbamodithioates in the presence of DBU giving 1,2,4-triazole-5-thiones (18, 19, 39-47). Two of final products (39, 40) were undergone alkylation in alkaline solution to appropriate sulfides (48-53). Then methylsulfides (48, 49) were oxidized with peroxyacetic acid to sulfoxides (54, 55). The obtained compounds were tested in vitro towards Mycobacterium tuberculosis.
• Synthesis and Reactions of Some New Quinoline Thiosemicarbazide Derivatives of Potential Biological Activity
  作者：E. M. Keshk、S. I. El-Desoky、M. A. A. Hammouda、A. H. Abdel-Rahman、A. G. Hegazi

  DOI：10.1080/10426500701641304

  日期：2008.5.14

  Quinoline-2-carbohydrazide (3) was reacted with aryl or alkyl isothiocyanates to give the corresponding quinoline thiosemicarbazides (4a-e). Cyclization of the substituted thiosemicarbazides with sodium hydroxide led to the formation of 5-(quinolin-2-yl)-2H-1, 2, 4-triazole-3(4H)-thiones (5a-e). Desulfurization of thiosemicarbazides by mercuric oxide gave 5-(quinolin-2-yl)-1, 3, 4-oxadiazol- 2-amines (6a-e). Treatment of thiosemicarbazides with ethyl bromoacetate or -bromopropionic acid yielded (Z)-N'-(3-substituted thiazolidin-4-oxo-2-ylidene) quinoline-2-carbohydrazides (7a-d), (8a-d), respectively. Treatment of thiosemicarbazides with chloroacetone furnished (Z)-N'-(4-methyl-3-substituted-thiazol-2(3H)-ylidene) quinoline-2-carbohydrazides (9a-d). Furthermore, the reaction of thiosemicarbazides with phosphorus oxychloride gave N-substituted-5-(quinolin-2-yl)-1,3,4-thiadiazol-2-amines (10a-e). All newly synthesized compounds were tested and evaluated for antimicrobial activity.