6,7-dihydro-9-(2,4-dimethoxyphenyl)-6,6-dimethyl-[1,2,4]triazolo[5,1-b]quinazolin-8(4H,5H,9H)-one | 500267-19-6

• 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: 6,7-dihydro-9-(2,4-dimethoxyphenyl)-6,6-dimethyl-[1,2,4]triazolo[5,1-b]quinazolin-8(4H,5H,9H)-one
• 英文别名: 9-(2,4-dimethoxyphenyl)-6,6-dimethyl-1,5,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8-one
• CAS: 500267-19-6
• 化学式: C₁₉H₂₂N₄O₃
• 分子量: 354.409
• InChiKey: CJRDNIFOBWHYCU-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 、 2,4-二甲氧基苯甲醛 在 溶剂黄146 作用下， 反应 0.5h， 以88%的产率得到6,7-dihydro-9-(2,4-dimethoxyphenyl)-6,6-dimethyl-[1,2,4]triazolo[5,1-b]quinazolin-8(4H,5H,9H)-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

• Nano-SiO2: a green, efficient, and reusable heterogeneous catalyst for the synthesis of quinazolinone derivatives
  作者：Mir Rasul Mousavi、Malek Taher Maghsoodlou

  DOI：10.1007/s13738-014-0533-4

  日期：2015.5

  A highly efficient and general method is applied for the multicomponent synthesis of quinazolinone derivatives from cyclocondensation of aromatic aldehydes and dimedone with 2-amino benzimidazole or 3-amino-1,2,4-triazole using nano-SiO2 as a catalyst in acetonitrile at room temperature. In this method, nano-SiO2 was used as a green and reusable catalyst. This synthetic method provides several advantages

  一种高效，通用的方法，是利用纳米SiO 2作为催化剂，在2-乙氧基苯并咪唑或3-氨基-1,2,4-三唑的催化作用下，由芳香醛和二甲酮与2-氨基苯并咪唑或3-氨基-1,2,4-三唑进行环缩合而合成喹唑啉酮衍生物室内温度。在此方法中，纳米SiO 2被用作绿色可重复使用的催化剂。这种合成方法具有许多优点，包括产率高，反应时间短，后处理简单，条件温和且价格便宜，绿色且可回收。
• A simple, convenient one-pot synthesis of [1,2,4]triazolo/benzimidazolo quinazolinone derivatives by using molecular iodine
  作者：Ravinder Goud Puligoundla、Shuklachary Karnakanti、Rajashaker Bantu、Kommu Nagaiah、Sudhakar Babu Kondra、Lingaiah Nagarapu

  DOI：10.1016/j.tetlet.2013.02.099

  日期：2013.5

  A wide variety of quinazolinone derivatives have been synthesized by condensation of 3-amino-1,2,4-trazole and 2-aminobenzimidazole as amine sources, with aromatic aldehydes and dimedone in the presence of 10 mol % of molecular iodine in acetonitrile under reflux conditions through one-pot reactions. Environmental acceptability, low cost, no need of chromatographic separation, and high yields are the important features of this protocol. (C) 2013 Elsevier Ltd. All rights reserved.
• Catalytic systems containing p-toluenesulfonic acid monohydrate catalyzed the synthesis of triazoloquinazolinone and benzimidazoquinazolinone derivatives
  作者：Mir Rasul Mousavi、Malek Taher Maghsoodlou

  DOI：10.1007/s00706-014-1273-y

  日期：2014.12

  A variety of quinazolinones are readily prepared via one-pot three-component reaction in good to excellent yields. The desired products were obtained from the reaction of dimedone, various aldehydes with 2-aminobenzimidazole or 3-amino-1,2,4-triazole under mild reaction conditions using p-toluenesulfonic acid monohydrate as effective catalyst in acetonitrile as solvent. Starting from the corresponding available materials, this friendly and environmentally free-metal procedure has been successfully extended to the synthesis of triazoloquinazolinones and benzimidazoquinazolinones. The salient advantages of this method are mild reaction conditions, nontoxic and inexpensive catalyst, environmentally benign, high to excellent yields, shorter reaction times, easy operation, and no column chromatographic separation.