9-(4-methylphenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one | 948141-77-3

• 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-(4-methylphenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one
• 英文别名: 7,7-dimethyl-4-p-tolyl-4,7,8,9-tetrahydro-6H-1,2,3,3a,9-pentaaza-cyclopenta[b]naphthalen-5-one；6,6-Dimethyl-9-(4-methylphenyl)-4,5,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8-one；6,6-dimethyl-9-(4-methylphenyl)-4,5,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8-one
• CAS: 948141-77-3
• 化学式: C₁₇H₁₉N₅O
• 分子量: 309.371
• InChiKey: MJNBEDLUFKNQEE-UHFFFAOYSA-N

物化性质

• 沸点：
  504.1±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(4-methylphenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one 、 氯乙酸乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以83.7%的产率得到(7,7-dimethyl-5-oxo-4-p-tolyl-5,6,7,8-tetrahydro-4H-1,2,3,3a,9-pentaaza-cyclopenta[b]naphthalen-9-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  [EN] PYRAZOL[1,5-a]PYRIMIDINE DERIVATIVES AS WNT PATHWAY ANTAGONISTS
  [FR] DÉRIVÉS DE PYRAZOLO[1,5-A]PYRIMIDINE COMME ANTAGONISTES DE LA VOIE WNT

  摘要：

  根据通用式（I），其中X1为CR1或N；X2为CR2或N；X3为CR3或N；其中至少一个来自X1、X2和X3中的N组；Z为CR4或CR4R5；Y为N或NR6；虚线表示1或2个双键；L为O或NR7；每个A独立地来自CR8R8a，它们相同或不同，其中一个A可选自O、S、NR9、S(O)和S(0)2组；n为2至4；它们的溶剂化合物、水合物、酯和药学上可接受的盐，它们用于调节Wnt信号通路活性以及作为药物使用，优选用于癌症治疗。

  公开号：

  WO2011121096A1
• 作为产物：
  描述：

  7,7-dimethyl-4-(4-methylphenyl)-2-thioxo-2,3,4,6,7,8-hexahydro-5(1H)-quinazolinone 在 sodium azide 、 mercury(II) diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以71%的产率得到9-(4-methylphenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-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

• Three-Component Reaction of Dimedone with Aromatic Aldehydes and 5-Aminotetrazole
  作者：V. L. Gein、A. N. Prudnikova、A. A. Kurbatova、M. V. Dmitriev、V. V. Novikova、I. P. Rudakova、A. L. Starikov

  DOI：10.1134/s1070363219050049

  日期：2019.5

  Reactions of dimedone with aromatic aldehyde and 5-aminotetrazole monohydrate proceeded with the formation of 9-aryl-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazoline-8(4H)-ones or 9-aryl-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-diones depending on the nature of substituent in aromatic aldehyde. Antimicrobial, antifungal and analgesic activities of the synthesized compounds

  二甲酮与芳族醛和5-氨基四唑一水合物的反应进行，形成9-芳基-6,6-二甲基-5,6,7,9-四氢四唑[5,1- b ]喹唑啉-8（4 H）-一或9-芳基-3,3,6,6-四甲基-3,4,6,7-四氢-2 H--吨-1,8（5 H，9 H）-二酮，具体取决于取代基的性质芳香醛。研究了合成化合物的抗菌，抗真菌和止痛活性。
• Al(III) chloride catalyzed multi-component domino strategy: Synthesis of library of dihydrotetrazolo[1,5- a ]pyrimidines and tetrahydrotetrazolo[1,5- a ]quinazolinones
  作者：Parteek Kour、Varun P. Singh、Brijmohan Khajuria、Tajinder Singh、Anil Kumar

  DOI：10.1016/j.tetlet.2017.09.052

  日期：2017.11

  Tetrazolo[1,5-a]pyrimidines are well recognized and valuable scaffolds in drug discovery. In the current manuscript, we demonstrated AlCl3 catalyzed synthesis of series of dihydrotetrazolo[1,5-a]pyrimidines and tetrahydrotetrazolo[1,5-a]quinazolinones via a modified Biginelli type multi-component reaction of 5-aminotetrazole, aldehyde and diverse active methylene components such as acetophenone/al

  Tetrazolo [1,5- a ]嘧啶是药物发现中公认的有价值的支架。在当前的手稿中，我们证明了AlCl 3通过5-氨基四唑，醛和多种多样的修饰的Biginelli型多组分反应，催化合成一系列二氢四唑并[1,5- a ]嘧啶和四氢四唑并[1,5- a ]喹唑啉酮。活性亚甲基组分，如苯乙酮/乙酰乙酸烷基酯/二甲酮。这提供了直接从容易获得的起始原料直接构建高度官能化的二氢四唑并[1,5- a ]嘧啶和四氢四唑并[1,5- a ]喹唑啉酮的有效途径。
• 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.