3-oxo-6-phenyl-2,3-dihydropyridazine-4-carbonitrile | 87769-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-oxo-6-phenyl-2,3-dihydropyridazine-4-carbonitrile
• 英文别名: 6-phenyl-4-cyano-3(2H)-pyridazinone；2,3-Dihydro-3-oxo-6-phenyl-4-pyridazinecarbonitrile；6-oxo-3-phenyl-1H-pyridazine-5-carbonitrile
• CAS: 87769-57-1
• 化学式: C₁₁H₇N₃O
• 分子量: 197.196
• InChiKey: NRYOZBWIZLLHGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N'-(1-phenylethylidene)cyanoacetohydrazide 在 碘 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以60%的产率得到3-oxo-6-phenyl-2,3-dihydropyridazine-4-carbonitrile
  参考文献：
  名称：

  氰基乙酸酰肼：一种合成多官能吖嗪和唑类衍生物的有效途径

  摘要：

  AbstractHerein, the synthesis of nitrogen‐containing heterocyclic scaffolds from heterocyclization of cyanoacetic acid hydrazide derivatives is described. Thiosemicarbazide derivative1aundergoes base‐mediated cyclization producing pyrazole derivative of type2. The triazolopyridine5was obtained by double cyclization of1aand benzylidene malononitrile. Compound1bcondensed with ethyl chloroformate to furnish pyrazolooxazine8. Compound1bwas added to benzoyl isothiocyanate under thermal condition to form oxadiazine derivative10while, keeping the above reactant under room temperature to form acyclic derivative11. Using CS2as a cyclizing agent for compound1byielded pyrazole derivative13. Treatment of1bwith I2resulted in oxidative cyclization producing pyridazine derivative14. Compound1ccyclized with benzoyl isothiocyanate forming triazolothiazine derivative18. While using cinnamoyl isothiocyanate, the acyclic product22was obtained. Compound1cwas condensed with formaldehyde leading to oxadiazole derivative25.

  DOI：

  10.1002/jhet.3926

文献信息

• A Regioselective One-Pot, Three Component Synthesis of 6-Aryl-4-cyano-3(2H)-pyridazinones in Water
  作者：Mehdi Rimaz、Jabbar Khalafy、Peyman Najafi Moghadam

  DOI：10.1071/ch09602

  日期：——

  A series of 4-cyano-3(2H)-pyridazinones bearing different aryl substituents in the 6-position of the pyridazinone ring was synthesized regioselectively using a novel efficient one-pot three component reaction of alkyl 2-cyanoacetates with arylglyoxals in the presence of hydrazine hydrate at room temperature in water.

  在室温水中，利用 2-氰基乙酸烷基酯与芳基乙二醛在水合肼存在下发生的新型高效单锅三组分反应，选择性地合成了一系列在哒嗪酮环的 6 位具有不同芳基取代基的 4-氰基-3(2H)-哒嗪酮。
• Polyfunctional Nitriles in Organic Syntheses: A Novel Route to Aminopyrroles, Pyridazines and Pyrazolo[3,4-c]pyridazines
  作者：Saleh Al-Mousawi、Moustafa Sherief Moustafa、Herbert Meier、Heinz Kolshorn、Mohamed Hilmy Elnagdi

  DOI：10.3390/molecules14020798

  日期：——

  Phenacylmalononitrile 1 reacts with dimethylformamide dimethyl acetal to yield an enaminone which could be readily converted into a pyrrole or an aminopyridazine by treating with ammonium acetate and hydrazine hydrate, respectively. Compound 1 reacted with hydrazine hydrate in ethanol at room temperature to yield the dihydropyridazine 9 as a single product. In refluxing ethanol this product further

  苯酰基丙二腈 1 与二甲基甲酰胺二甲基乙缩醛反应生成烯胺酮，通过分别用乙酸铵和水合肼处理，可以很容易地将其转化为吡咯或氨基哒嗪。在室温下，化合物 1 在乙醇中与水合肼反应，得到二氢哒嗪 9，为单一产物。在回流乙醇中，该产物进一步与水合肼反应，得到新型二氢吡唑并哒嗪胺 10。
• Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents
  申请人：Warner-Lambert Company

  公开号：US04404203A1

  公开（公告）日：1983-09-13

  Substituted 6-phenyl-3(2H)-pyridazinone compounds are useful as cardiotonic agents. Said compounds cause a significant increase in myocardial contractility in the anesthetized dog. Said compounds are produced by reacting substituted benzoylpropionic acids with suitably substituted hydrazines to provide 6-phenyl-4,5-dihydro-3(2H)-pyridazinones which are dehydrogenated to the desired product. The intermediate 6-phenyl-4,5-dihydro-3(2H)-pyridazinones are themselves useful as cardiotonic agents.

  取代的6-苯基-3(2H)-吡啶酮化合物可用作心脏强效剂。该化合物在麻醉犬的心肌收缩力中引起显著增加。该化合物是通过将取代的苯甲酰丙酸与适当取代的肼反应得到6-苯基-4,5-二氢-3(2H)-吡啶酮，然后脱氢得到所需产物。中间体6-苯基-4,5-二氢-3(2H)-吡啶酮本身也可用作心脏强效剂。
• WERMUTH, CAMILLE-GEORGES;SCHLEWER, GILBERT;BOURGUIGNON, JEAN-JACQUES;MAGH+, J. MED. CHEM., 32,(1989) N, C. 528-537
  作者：WERMUTH, CAMILLE-GEORGES、SCHLEWER, GILBERT、BOURGUIGNON, JEAN-JACQUES、MAGH+

  DOI：——

  日期：——
• US4404203A
  申请人：——

  公开号：US4404203A

  公开（公告）日：1983-09-13