2-amino-3,4-dimethyl-N'-phenylbenzohydrazide | 1600519-94-5

• 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: 2-amino-3,4-dimethyl-N'-phenylbenzohydrazide
• CAS: 1600519-94-5
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: FXKNUKXAFPICQF-UHFFFAOYSA-N

物化性质

• 沸点：
  427.6±45.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯丙炔醛缩二乙醛 、 2-amino-3,4-dimethyl-N'-phenylbenzohydrazide 在 caesium carbonate 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以85%的产率得到5,6-dimethyl-1,2-diphenylpyrazolo[5,1-b]quinazolin-9(1H)-one
  参考文献：
  名称：

  Copper(I)-catalyzed synthesis of 1-arylpyrazolo[5,1-b]quinazolin-9(1H)-one via intramolecular alkyne hydroamination

  摘要：

  The 1-arylpyrazolo[5,1-b]quinazolin-9(1H)-one derivatives were obtained via intramolecular alkyne hydroamination reaction of 2-amino-N'-arylbenzohydrazide and alkynal diethyl acetal in the presence of CuBr and Cs2CO3. This new procedure provides an efficient method to construct fused tricyclic heterocycle containing both pyrazole and quinazoline analogues. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.048

文献信息

• Copper(I)-catalyzed synthesis of thienopyrazoloquinazolinone derivatives under ligand-free conditions
  作者：Wen-Ting Zhang、Dong-Sheng Chen、Mei-Mei Zhang、Xiang-Shan Wang

  DOI：10.1007/s11164-016-2497-8

  日期：2016.8

  synthesized by reaction of 2-aminobenzohydrazide and 3-bromothiophene-2-carbaldehyde in good yields. The reaction includes subsequent condensation, cyclization, and CuBr-catalyzed Ullmann-type reaction under ligand-free conditions. Graphical Abstract

  摘要 通过2-氨基苯甲酰肼与3-溴噻吩-2-的反应合成了一系列稠合的四环噻吩并[3'，2'：3,4]吡唑并[5,1- b ]喹唑啉-6（4 H）-一衍生物。甲醛收率高。该反应包括随后的缩合，环化和在无配体的条件下CuBr催化的Ullmann型反应。 图形概要
• The Chemo-selective Reaction of 2-Amino-<i>N′</i> -arylbenzohydrazide and Ketonic Acid Catalyzed by Iodine for the Synthesis of Quinazoline Derivatives
  作者：Jian-Quan Liu、Wen-Ting Zhang、Xiang-Shan Wang

  DOI：10.1002/jhet.3228

  日期：2018.8

  The chemo‐selective reaction of 2‐amino‐N′‐arylbenzohydrazide and ketonic acid catalyzed by iodine was used to synthesize various 2,3‐dihydroquinazolin‐4(1H)‐ones efficiently. The use of levulinic acid furnished a series of 2,3,3a,4‐tetrahydropyrrolo[1,2‐a]quinazoline‐1,5‐diones in high yields, while acetobutyric acid only afforded the quinazoline skeletons without forming the second pyridine ring

  碘催化2-氨基N'-芳基苯并肼与酮酸的化学选择性反应可有效合成各种2,3-二氢喹唑啉-4（1 H）-酮。乙酰丙酸的使用可高收率地提供一系列2,3,3 a，4-四氢吡咯并[1,2- a ]喹唑啉-1,5-二酮，而乙酰丁酸仅提供了喹唑啉骨架而未形成第二个吡啶戒指。使用醇代替离子液体作为溶剂，随后以一锅法对乙酰丁酸底物的羧基进行酯化反应。
• Copper-catalyzed synthesis of 1-amino-5-arylindazolo[3,2- b ]quinazolin-7(5 H )-ones via a ring-opening reaction of 4-halogenated isatin
  作者：Yong-Gang Ma、Chao Li、Chang-Sheng Yao、Xiang-Shan Wang

  DOI：10.1016/j.tet.2016.05.013

  日期：2016.7

  The domino reaction of 4-halogenated isatins and 2-amino-N′-arylbenzohydrazides catalyzed by CuI in the presence of Cs2CO3 is described. A possible reaction mechanism containing the consecutive condensation, cyclization, C–N bond Ullmann coupling, ring-opening and decarboxylation is put forward according to the control experiments. This procedure provides an efficient method for the synthesis of fused

  描述了CuI在Cs 2 CO 3存在下4-卤代靛红与2-氨基-N'-芳基苯并酰肼的多米诺反应。根据控制实验，提出了可能的反应机理，包括连续缩合，环化，C–N键乌尔曼偶合，开环和脱羧。该程序提供了一种高效合成高产率的稠合多环1-氨基-5-芳基吲哚并[3,2 - b ]喹唑啉-7（5 H）-ones衍生物的有效方法。
• An efficient synthesis of quinazoline or pyrrolo[1,2-a]quinazolin-5(1H)-one derivatives in ionic liquids catalyzed by iodine
  作者：Jian-Quan Liu、Fang Dong、Wen-Ting Zhang、Xiang-Shan Wang

  DOI：10.1007/s11164-017-3020-6

  日期：2017.12

  iodine-catalyzed reaction of 2-amino-N′-arylbenzohydrazides and haloketones was carried out in ionic liquids and was found in good chemoselectivity. 5-Chloropentan-2-one selectively gave fused pyrrolo[1,2-a]quinazolin-5(1H)-one derivatives, and 6-chlorohexan-2-one only formed simple quinazolin-4(1H)-ones, while the second cyclization did not take place at all. Graphical Abstract

  摘要 2-氨基-N'-芳基苯甲酰肼与卤代酮的碘催化反应在离子液体中进行，发现具有良好的化学选择性。5-氯opentan-2-one有选择地生成稠合的吡咯并[1,2- a ]喹唑啉-5（1 H）-one衍生物，而6-氯己酮-2-one仅形成简单的喹唑啉-4（1 H）-one，而第二个环化根本没有发生。 图形概要
• Domino synthesis of fused pyrazolo[5,1- b ]quinazolin-9(1 H )-ones catalyzed by CuI via subsequent Michael addition and elimination
  作者：Yan Zhang、Jing Xu、Chao Li、Xiang-Shan Wang

  DOI：10.1016/j.tet.2015.09.055

  日期：2015.11

  A Domino reaction of 2-aminobenzohydrazides and 2-bromocinnamaldehydes is treated in the presence of CuI and Cs2CO3, and gives unexpected pyrazolo[5,1-b]quinazolin-9(1H)-one derivatives in good yields. A possible mechanism containing subsequent Michael addition and elimination is proposed to explain the formation of the pyrazole ring. This new procedure has the advantages of one-pot, available reactant, and milder conditions. (C) 2015 Elsevier Ltd. All rights reserved.