6,6-dimethyl-9-(3-nitrophenyl)-1,5,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8-one | 325830-54-4

• 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: 6,6-dimethyl-9-(3-nitrophenyl)-1,5,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8-one
• CAS: 325830-54-4
• 化学式: C₁₆H₁₆N₆O₃
• 分子量: 340.341
• InChiKey: LMFPLYATWHOPMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7,7-dimethyl-4-(3-nitrophenyl)-2-thioxo-2,3,4,6,7,8-hexahydroquinazolin-5(1H)-one 在 sodium azide 、 mercury(II) diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以65%的产率得到6,6-dimethyl-9-(3-nitrophenyl)-1,5,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8-one
  参考文献：
  名称：

  One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide

  摘要：

  An novel, versatile and cost-effective approach for tetrazolo[1,5-a]pyrimidines and tetrazolo[1,5-a]quinazolines from cyclization reaction of dihydropyrimidinethiones with sodium azide in the presence of mercuric acetate is described. To compare this procedure with the conventional method, we carried out the cyclization reactions through direct functionalization of the pyrimidinethione core, which obtained from Biginelli 3,4-dihydropyrimidine-2-thiones or 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones.

  DOI：

  10.3987/com-11-12351

文献信息

• Sustainable design and novel synthesis of highly recyclable magnetic carbon containing aromatic sulfonic acid: Fe ₃ O ₄ @C/Ph—SO ₃ H as green solid acid promoted regioselective synthesis of tetrazoloquinazolines
  作者：Asadollah Hassankhani、Behnam Gholipour、Sadegh Rostamnia、Elham Zarenezhad、Nasrin Nouruzi、Taras Kavetskyy、Rovshan Khalilov、Mohammadreza Shokouhimehr

  DOI：10.1002/aoc.6346

  日期：2021.10

  Fe3O4@meso-C immobilized with activated 4-aminobenzenesulfonic acid to achieve Fe3O4@C/Ph—SO3H. Structural, physico-chemical, and magnetic properties of synthesized Fe3O4@C/Ph—SO3H catalyst using various analyses such as FT-IR spectroscopy, TGA, XRD, SEM, TEM. EDX, and VSM were investigated. Fe3O4@C/Ph—SO3H was used as a stable and recoverable acid catalyst for regioselective three-component synthesis of

  制备了封装在多孔碳壳中的绿色且稳定的磁性 Fe 3 O 4核。然后，合成的 Fe 3 O 4 @meso-C 表面固定有活化的 4-氨基苯磺酸以获得 Fe 3 O 4 @C/Ph-SO 3 H。合成 Fe 的结构、物理化学和磁性3 O 4 @C/Ph-SO 3 H 催化剂使用各种分析，如 FT-IR 光谱、TGA、XRD、SEM、TEM。研究了 EDX 和 VSM。Fe 3 O 4 @C/Ph—SO 3H 用作稳定且可回收的酸催化剂，用于在温和条件下区域选择性三组分合成四唑并喹唑啉。由于具有活性 SO 3 H 基团，该催化剂提供了一种一次性的绿色方案，在温和条件下反应，产率高，并且能够回收和再利用而不会显着降低活性。
• An efficient regioselective three-component synthesis of tetrazoloquinazolines using g-C3N4 covalently bonded sulfamic acid
  作者：Asadollah Hassankhani、Behnam Gholipour、Sadegh Rostamnia

  DOI：10.1016/j.poly.2019.114217

  日期：2020.1

  A green and cost-effective protocol developed using covalently bonded sulfamic acid graphitic carbon nitride (g-C3N4/NHSO3H) for the synthesis of quinazoline derivatives using three-component condensation reaction of benzaldehyde, 2-aminotetrazole and dimedone. The XRD, TEM, SEM, EDX and FT-IR techniques were used to identify the physical and chemical properties of g-C3N4/NHSO3H. The -NHSO3H solid catalyst, was reused eight times without significant decrease in activity. This catalyst acts as a benign acid catalyst, a green protocol of a one-pot due to having significant advantages such as active sites containing SO3H groups, reacting under mild conditions with high efficiency as well as the ability to recover and reuse without decreasing activity. (C) 2019 Elsevier Ltd. All rights reserved.
• One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide
  作者：Xi-Cun Wang、Ying Wei、Yu-Xia Da、Zhang Zhang、Zheng-Jun Quan

  DOI：10.3987/com-11-12351

  日期：——

  An novel, versatile and cost-effective approach for tetrazolo[1,5-a]pyrimidines and tetrazolo[1,5-a]quinazolines from cyclization reaction of dihydropyrimidinethiones with sodium azide in the presence of mercuric acetate is described. To compare this procedure with the conventional method, we carried out the cyclization reactions through direct functionalization of the pyrimidinethione core, which obtained from Biginelli 3,4-dihydropyrimidine-2-thiones or 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones.