4H,6H-[1,2,3]triazolo[1,5-a][1,4]benzodiazepine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 4H,6H-[1,2,3]triazolo[1,5-a][1,4]benzodiazepine
• 英文别名: 5,6-dihydro-4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepine；5,6-dihydro-4H-triazolo[1,5-a][1,4]benzodiazepine
• 化学式: C₁₀H₁₀N₄
• 分子量: 186.216
• InChiKey: VOSCFERCKGVMHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4H,6H-[1,2,3]triazolo[1,5-a][1,4]benzodiazepine 、 天然芥菜籽油 以 二氯甲烷 为溶剂， 以99%的产率得到N-allyl-4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepine-5(6H)-carbothioamide
  参考文献：
  名称：

  Application of a Sequential Multicomponent Assembly Process/Huisgen Cycloaddition Strategy to the Preparation of Libraries of 1,2,3-Triazole-Fused 1,4-Benzodiazepines

  摘要：

  A strategy featuring a multicomponent assembly process followed by an intramolecular azide-alkyne dipolar (Huisgen) cycloaddition was implemented for the facile synthesis of three different 1,2,3-triazolo-1,4-benzodiazepine scaffolds. A diverse library of 170 compounds derived from these scaffolds was then created through N-functionalizations, palladium catalyzed cross coupling reactions, and several applications of alpha-aminonitrile chemistry.

  DOI：

  10.1021/co2002087
• 作为产物：
  描述：

  2-azidobenzyl alcohol 在 sodium tetrahydroborate 、 氨 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 4H,6H-[1,2,3]triazolo[1,5-a][1,4]benzodiazepine
  参考文献：
  名称：

  [1,2,3]三唑[1,5- a ] [1,4]苯并二氮杂s的模块化和灵活的新方法

  摘要：

  描述了获得[1,2,3]三唑并[1,5- a ] [1,4]苯并二氮杂和其他衍生物的新合成途径。该策略基于将2-氧代亚烷基亚膦酰基环酮加成至o-官能化的芳基叠氮化物，然后使相应的三唑中间体与胺反应。这种新方法具有独特的性质，例如区域选择性，模块性，温和的反应条件和高收率。

  DOI：

  10.1016/j.tetlet.2007.03.121

文献信息

• Novel substituted triazolo benzodiazepine scaffolds to explore chemical space
  作者：Gayan A. Abeykoon、James J. Sahn、Stephen F. Martin

  DOI：10.1016/j.tetlet.2021.152828

  日期：2021.3

  process to give an intermediate azido alkyne that undergoes a facile Huisgen dipolar cycloaddition. The triazolo-1,4-benzodiazepines thus produced may be endowed with aryl halide, secondary amino, alcohol, aldehyde or carboxylic acid groups as functional handles for orthogonal derivatization reactions. Modification of this approach enabled the facile synthesis of the related triazolo-1,4-benzodiazepin-6-ones

  描述了高效，简明的路线，获取了新颖的三唑并-1,4-苯并二氮杂sc骨架，这些骨架经过适当的官能化处理，可以在三个位置进行多样化，以探索具有不同取代基的三维空间。这些支架的一种方法具有简化的多组分组装过程，可得到中间体叠氮基炔烃，该中间体可进行简单的惠斯根偶极环加成反应。如此产生的三唑并1,4-苯并二氮杂may可被赋予芳基卤，仲氨基，醇，醛或羧酸基团作为正交衍生化反应的功能性处理。对该方法的改进使得可以容易地合成相关的三唑-1,4-苯并二氮杂-6-酮，也带有三个功能性手柄。
• Synthesis and Diversification of 1,2,3-Triazole-Fused 1,4-Benzodiazepine Scaffolds
  作者：James R. Donald、Stephen F. Martin

  DOI：10.1021/ol1028404

  日期：2011.3.4

  A substituted heterocyclic scaffold comprising a 1,4-benzodiazepine fused with a 1,2,3-triazole ring has been synthesized and diversified via a variety of refunctionalizations. The strategy features the rapid assembly of the scaffold by combining 3−4 reactants in an efficient multicomponent assembly process, followed by an intramolecular Huisgen cycloaddition.

  包含与 1,2,3-三唑环稠合的 1,4-苯二氮卓类的取代杂环支架已通过各种再官能化合成和多样化。该策略的特点是通过在高效的多组分组装过程中组合 3-4 种反应物，然后进行分子内的 Huisgen 环加成，从而快速组装支架。
• Application of a Sequential Multicomponent Assembly Process/Huisgen Cycloaddition Strategy to the Preparation of Libraries of 1,2,3-Triazole-Fused 1,4-Benzodiazepines
  作者：James R. Donald、Rebekah R. Wood、Stephen F. Martin

  DOI：10.1021/co2002087

  日期：2012.2.13

  A strategy featuring a multicomponent assembly process followed by an intramolecular azide-alkyne dipolar (Huisgen) cycloaddition was implemented for the facile synthesis of three different 1,2,3-triazolo-1,4-benzodiazepine scaffolds. A diverse library of 170 compounds derived from these scaffolds was then created through N-functionalizations, palladium catalyzed cross coupling reactions, and several applications of alpha-aminonitrile chemistry.
• A new modular and flexible approach to [1,2,3]triazolo[1,5-a][1,4]benzodiazepines
  作者：Mateo Alajarín、José Cabrera、Aurelia Pastor、José M. Villalgordo

  DOI：10.1016/j.tetlet.2007.03.121

  日期：2007.5

  A new synthetic route for the access to [1,2,3]triazolo[1,5-a][1,4]benzodiazepines and other derivatives is described. This strategy is based on the cycloaddition of 2-oxoalkylidenephosphoranes to o-functionalized aryl azides followed by the reaction of the corresponding triazole intermediate with amines. This new approach presents unique properties such as regioselectivity, modularity, mild reaction

  描述了获得[1,2,3]三唑并[1,5- a ] [1,4]苯并二氮杂和其他衍生物的新合成途径。该策略基于将2-氧代亚烷基亚膦酰基环酮加成至o-官能化的芳基叠氮化物，然后使相应的三唑中间体与胺反应。这种新方法具有独特的性质，例如区域选择性，模块性，温和的反应条件和高收率。