9-(2,3-dimethoxyphenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 9-(2,3-dimethoxyphenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one
• 英文别名: 6,7-dihydro-9-(2,3-dimethoxyphenyl)-6,6-dimethyl-[1,2,4]triazolo[5,1-b]quinazolin-8(4H,5H,9H)-one；9-(2,3-dimethoxyphenyl)-6,6-dimethyl-1,5,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8-one
• 化学式: C₁₉H₂₂N₄O₃
• 分子量: 354.409
• InChiKey: QUJXNAFKMXNNIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氨基-1,2,4-三氮唑 、 5,5-二甲基-1,3-环己二酮 、 2,3-二甲氧基苯甲醛 在 溶剂黄146 作用下， 反应 0.33h， 以98%的产率得到9-(2,3-dimethoxyphenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one
  参考文献：
  名称：

  A simple, economical, and environmentally benign protocol for the synthesis of [1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one and hexahydro[4,5]benzimidazolo[2,1-b]quinazolinone derivatives

  摘要：

  本研究描述了一种高效合成[1,2,4]三唑并[5,1-b]喹唑啉-8(4H)-酮和六氢[4,5]苯并咪唑并[2,1-b]喹唑啉酮衍生物的方法，并且产量很高。该方法是以乙酸为反应介质，在 60 ℃ 下进行醛、二甲基酮和 3-氨基-1,2,4-三唑或 2-氨基苯并咪唑的三组分反应。我们发现，使用乙酸作为反应介质会对反应产生显著的有利影响，使反应无需加入催化剂即可进行，而其他类似方法则需要加入催化剂。这种方法的显著优点是产率高、反应时间短、反应条件温和、材料更容易获得且价格低廉、更环保、无需柱层析以及操作步骤简单。

  DOI：

  10.1007/s13738-015-0609-9

文献信息

• Heterogeneous AlPO4(SO3H) nanosheets: novel catalyst for the multi-component synthesis of quinazolinones and highly functionalized piperidines
  作者：Hashem Sharghi、Jasem Aboonajmi、Mahdi Aberi、Pezhman Shiri

  DOI：10.1007/s13738-018-1308-0

  日期：2018.5

  AbstractNanosheets AlPO4(SO3H) as a highly active solid acid catalyst were prepared and characterized. The morphology of obtained catalyst exhibited nanosheets with ∼ 25–35 nm thickness. The heterogeneous nanocatalyst was characterized by FT-IR, EDX, and FE-SEM analysis. The nanosulfonated-AlPO4 were found useful for cyclization synthesis of highly functionalized piperidines and quinazolinones derivatives

  摘要制备并表征了作为高活性固体酸催化剂的纳米片AlPO 4（SO 3 H）。获得的催化剂的形态显示出约25–35 nm厚度的纳米片。通过FT-IR，EDX和FE-SEM分析表征了多相纳米催化剂。纳米磺化AlPO 4已发现高收率的高收率可用于高官能化哌啶和喹唑啉酮衍生物的环化合成。显着的特征包括容易和快速分离产物，易于以低成本处理催化剂，无需通过柱色谱法纯化以及温和的反应条件。另外，根据文献，我们的喹唑啉酮合成方法的另一个重要特征是合成了结构多样的分子。最后，新开发的催化系统避免使用有毒的金属催化剂，最多可重复使用5次，而没有明显的催化活性。 图形概要
• A simple, economical, and environmentally benign protocol for the synthesis of [1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one and hexahydro[4,5]benzimidazolo[2,1-b]quinazolinone derivatives
  作者：Mir Rasul Mousavi、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani

  DOI：10.1007/s13738-015-0609-9

  日期：2015.8

  An efficient synthesis of [1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one and hexahydro[4,5]benzimidazolo[2,1-b]quinazolinone derivatives with good yields is described. This method involves three-component reaction between aldehydes, dimedone, and 3-amino-1,2,4-triazole or 2-aminobenzimidazole in acetic acid as reaction medium at 60 °C. We have found that the use of acetic acid as reaction medium results in a remarkable beneficial effect on the reaction, allowing it to be performed without the need of incorporating a catalyst, which is the case in other similarly reported methodologies. The notable advantages of this protocol are excellent yields, short reaction time, mild reaction conditions, more readily available and inexpensive materials, more environmentally friendly, no need for column chromatography, and simple work-up procedure.

  本研究描述了一种高效合成[1,2,4]三唑并[5,1-b]喹唑啉-8(4H)-酮和六氢[4,5]苯并咪唑并[2,1-b]喹唑啉酮衍生物的方法，并且产量很高。该方法是以乙酸为反应介质，在 60 ℃ 下进行醛、二甲基酮和 3-氨基-1,2,4-三唑或 2-氨基苯并咪唑的三组分反应。我们发现，使用乙酸作为反应介质会对反应产生显著的有利影响，使反应无需加入催化剂即可进行，而其他类似方法则需要加入催化剂。这种方法的显著优点是产率高、反应时间短、反应条件温和、材料更容易获得且价格低廉、更环保、无需柱层析以及操作步骤简单。
• Green Synthesis of Benzoimidazopyrimidine, Benzimidazoloquinazolinone, Triazolopyrimidine and Triazoloquinazolinone Derivatives Catalyzed by Oxalic Acid Dihydrate
  作者：Seyed Sajad Sajadikhah、Bagher Liravi-Deylami

  DOI：10.2174/1570178618666210506120228

  日期：2022.3

  Benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine, and triazoloquinazolinone derivatives were synthesized via a one-pot multi-component reaction in the presence of a catalytic amount of oxalic acid dihydrate. The reactions were performed in the mixture of EtOH:H2O or under solvent-free conditions as green media. The advantageous features of these methodologies are inexpensive starting materials and catalyst, high atom economy and good yields, and metal-free synthesis. Moreover, all the products were obtained by simple filtration, and no need for column chromatography or tedious separation procedures, which is very important in terms of reducing environmental pollutions.

  摘要：通过一锅多组分反应，在草酸二水合物的催化下合成了苯并咪唑吡啶、苯并咪唑喹唑啉酮、三唑吡嗪和三唑喹唑啉酮衍生物。反应在EtOH:H2O混合物或无溶剂条件下进行，作为绿色介质。这些方法的优点是起始材料和催化剂廉价，原子经济性高，产率良好，且无金属合成。此外，所有产物均通过简单过滤得到，无需柱层析或繁琐的分离程序，这在减少环境污染方面非常重要。