3-chloro-6-[2-(4-nitrobenzylidene)hydrazinyl]pyridazine | 76953-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-6-[2-(4-nitrobenzylidene)hydrazinyl]pyridazine
• 英文别名: 4-Nitrobenzylidene-(6-chloro-3-pyridazinyl)-hydrazine；6-chloro-N-[(4-nitrophenyl)methylideneamino]pyridazin-3-amine
• CAS: 76953-25-8
• 化学式: C₁₁H₈ClN₅O₂
• 分子量: 277.67
• InChiKey: CFYXIAFKDLLULQ-UHFFFAOYSA-N

物化性质

• 熔点：
  277-279 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  516.7±50.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-chloro-6-[2-(4-nitrobenzylidene)hydrazinyl]pyridazine 、 吗啉 在 水 、 乙醇 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 24.0h， 以to give 5.6 g (85%) of the named compound的产率得到4-nitrobenzylidene-(6-morpholino-3-pyridazinyl)-hydrazine
  参考文献：
  名称：

  Process for the preparation of 6-(substituted

  摘要：

  本发明涉及一种新型制备6-(取代氨基)-3-吡啶嗪基肼的方法，其具有通式I 其中，R1代表氢原子或含有1至4个碳原子的烷基；R2和R3可以相同或不同，代表含有1至6个碳原子的烷基、含有2至6个碳原子的烯基、含有2至4个碳原子的羟基烷基、含有3至8个碳原子的环烷基、苯基或苄基，或者含有1至2个卤素原子、硝基、甲氧基或羟基的苯基、苄基或苯乙基；R2和R3中的一个也可以代表氢原子，或者R2和R3与相邻的氮原子一起也可以构成吗啡啶基、吡咯烷基、哌啶基、庚烷基亚甲基或N-甲基哌嗪基。该方法包括将具有通式II的化合物 其中，R1如上所定义，R4代表氯或溴原子或甲硫基，而A代表1,7,7-三甲基-2-双环(2,2,1)庚烯基或被R5基取代的苄亚甲基，其中R5代表氢、氯或溴原子，或甲氧基、硝基或甲基磺酰基基团，与具有通式III的胺反应 其中，R2和R3如上所定义，得到具有通式IV的化合物 其中，R1、R2、R3和A如上所定义，然后进行酸水解。由本发明新型方法制备的具有通式I的6-(取代氨基)-3-吡啶嗪基肼具有显著的降压作用，同时也可用作制备具有非常显著降压作用的6-(取代氨基)-3-吡啶嗪基肼的起始原料。

  公开号：

  US04329457A1
• 作为产物：
  描述：

  3-氯-6-肼基哒嗪 、 对硝基苯甲醛 以 乙醇 为溶剂， 反应 1.0h， 以52%的产率得到3-chloro-6-[2-(4-nitrobenzylidene)hydrazinyl]pyridazine
  参考文献：
  名称：

  Synthesis, Fungicidal and Antibacterial Activity of New Pyridazine Derivatives

  摘要：

  Compounds 1 - 3 were obtained in the reaction of 3,6-dichloropyridazines with phenylacetonitriles in the biphasic system - DMSO / 50% NaOH. The chlorine atom was replaced with cycloalkylamino (4 - 13) and hydrazinyl (23, 24) moiety. These last compounds were condensed with aldehydes (25 - 34). Pyridazynylphenylacetonitriles were converted into amides 14 - 18 and thioamides 19 - 22. In compounds 2, 3 the chlorine atom was replaced with thiophenyl (37, 38) and in compound 1 with thioethyl and thiophenyl (35, 36) functional groups. In the reactions of compounds 1, 2 with ammonium polysulfide thioamides with thiol group (39, 40) and chlorine atom (41, 42) were obtained. Compounds 1 - 17, 19 43 were screened for antibacterial and fungicidal activities.

  DOI：

  10.3987/com-08-11577

文献信息

• Synthesis, Fungicidal and Antibacterial Activity of New Pyridazine Derivatives
  作者：Henryk Foks、Krystyna Wisterowicz、Agnieszka Miszke、Kamil Brożewicz、Katarzyna Wiśniewska、Maria Dąbrowska-Szponar

  DOI：10.3987/com-08-11577

  日期：——

  Compounds 1 - 3 were obtained in the reaction of 3,6-dichloropyridazines with phenylacetonitriles in the biphasic system - DMSO / 50% NaOH. The chlorine atom was replaced with cycloalkylamino (4 - 13) and hydrazinyl (23, 24) moiety. These last compounds were condensed with aldehydes (25 - 34). Pyridazynylphenylacetonitriles were converted into amides 14 - 18 and thioamides 19 - 22. In compounds 2, 3 the chlorine atom was replaced with thiophenyl (37, 38) and in compound 1 with thioethyl and thiophenyl (35, 36) functional groups. In the reactions of compounds 1, 2 with ammonium polysulfide thioamides with thiol group (39, 40) and chlorine atom (41, 42) were obtained. Compounds 1 - 17, 19 43 were screened for antibacterial and fungicidal activities.
• Process for the preparation of 6-(substituted
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US04329457A1

  公开（公告）日：1982-05-11

  The invention relates to a novel process for the preparation of 6-(substituted amino)-3-pyridazinylhydrazines having the general formula I ##STR1## and their pharmaceutically acceptable acid addition salts, wherein R.sup.1 stands for hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms; R.sup.2 and R.sup.3 may be the same or different and stand for alkyl groups containing from 1 to 6 carbon atoms, alkenyl groups containing from 2 to 6 carbon atoms, hydroxyalkyl groups containing from 2 to 4 carbon atoms, cycloalkyl groups containing from 3 to 8 carbon atoms, phenyl or benzyl groups or phenyl, benzyl or phenylethyl groups containing one or two halogen atoms, nitro, methoxy or hydroxyl groups, and one of R.sup.2 and R.sup.3 may stand also for a hydrogen atom, or R.sup.2 and R.sup.3 together with the neighboring nitrogen atom may build up also a morpholino, pyrrolidino, piperidino, heptamethyleneimino or N-methylpiperazino group. The process consists in that a compound having the general formula II ##STR2## wherein R.sup.1 is as defined above, R.sup.4 stands for a chlorine or bromine atom or methylthio group, while A stands for a 1,7,7-trimethyl-2-bicyclo(2,2,1)heptylidene or a benzylidene group substituted by an R.sup.5 group, wherein R.sup.5 stands for hydrogen, chlorine or bromine atom, or a methoxy, nitro or methylsulphonyl group - is reacted with an amine having the general formula III R.sup.2 R.sup.3 NH (III) wherein R.sup.2 and R.sup.3 are as defined above - and the compound thus obtained having the general formula IV ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 and A are as defined above - is subjected to acidic hydrolysis. The 6-(substituted amino)-3-pyridazinylhydrazines having the general formula I and prepared by the novel process of invention, possess a significant hypotensive effect as well as they are used as starting materials for the preparation of 6-(substituted amino)-3-pyridazinylhydrazines having a very significant hypotensive action.

  本发明涉及一种新型制备6-(取代氨基)-3-吡啶嗪基肼的方法，其具有通式I 其中，R1代表氢原子或含有1至4个碳原子的烷基；R2和R3可以相同或不同，代表含有1至6个碳原子的烷基、含有2至6个碳原子的烯基、含有2至4个碳原子的羟基烷基、含有3至8个碳原子的环烷基、苯基或苄基，或者含有1至2个卤素原子、硝基、甲氧基或羟基的苯基、苄基或苯乙基；R2和R3中的一个也可以代表氢原子，或者R2和R3与相邻的氮原子一起也可以构成吗啡啶基、吡咯烷基、哌啶基、庚烷基亚甲基或N-甲基哌嗪基。该方法包括将具有通式II的化合物 其中，R1如上所定义，R4代表氯或溴原子或甲硫基，而A代表1,7,7-三甲基-2-双环(2,2,1)庚烯基或被R5基取代的苄亚甲基，其中R5代表氢、氯或溴原子，或甲氧基、硝基或甲基磺酰基基团，与具有通式III的胺反应 其中，R2和R3如上所定义，得到具有通式IV的化合物 其中，R1、R2、R3和A如上所定义，然后进行酸水解。由本发明新型方法制备的具有通式I的6-(取代氨基)-3-吡啶嗪基肼具有显著的降压作用，同时也可用作制备具有非常显著降压作用的6-(取代氨基)-3-吡啶嗪基肼的起始原料。