3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one | 23447-24-7

• 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: 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one
• 英文别名: 3a-Methyl-1,2,3,4-tetrahydropyrrolo[1,2-a]quinazolin-5-one
• CAS: 23447-24-7
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: FGOXZPKQFDIOAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(3-hydroxypropyl)-2-methyl-1,2,3,4-tetrahydro-4-quinazolinone 在 氯化铂 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one
  参考文献：
  名称：

  Gold- and Platinum-Catalyzed Formal Markownikoff’s Double Hydroamination of Alkynes: A Rapid Access to Tetrahydroquinazolinones and Angularly-Fused Analogues Thereof

  摘要：

  A highly efficient gold(I)- and platinum(II)-catalyzed process for formal Markownikoffs double hydroamination of alkynes tethered with hydroxyl group has been developed. The method was shown to be applicable to a broad range of 2-aminobenzamides and alkynols leading to the formation of multiply substituted tetrahydro-quinazolinones. Interestingly, when Pt(IV)Cl-4 catalyst was employed, cyclic angularly fused compound was obtained.

  DOI：

  10.1021/jo902293f

文献信息

• A Green Synthesis of Pyrrolo[1,2-<i>a</i>]quinazolin-5(1<i>H</i>)-one Derivatives in Ionic Liquids Catalyzed by Iodine
  作者：Jie-Xing Zhou、Lian Lu、Tuan-Jie Li、Chang-Sheng Yao、Xiang-Shan Wang

  DOI：10.1002/jhet.1768

  日期：2014.9

  A series of 2,3,3a,4‐tetrahydro‐3a‐methylpyrrolo[1,2‐a]quinazolin‐5(1H)‐one derivatives were synthesized by a reaction of 2‐aminobenzamide and 5‐chloropentan‐2‐one at 80 °C catalyzed by iodine in ionic liquid of [BMIm]Br. Compared with the other methods, this novel method has the advantages of milder reaction conditions, high yields, environmental benignity, and metal‐free catalyst.

  一系列的2,3,3一个，4-四氢-3-一个-methylpyrrolo [1,2一]喹唑啉-5（1 ħ） -酮衍生物通过的反应合成的2-氨基苯甲酰胺和5- chloropentan -2-碘在[BMIm] Br离子液体中在80°C催化-1。与其他方法相比，该新方法具有反应条件温和，收率高，环境友好和无金属催化剂的优点。
• Efficient and Convenient Synthesis of Pyrrolo[1,2-<i>a</i>]quinazoline Derivatives with the Aid of Tin(II) Chloride
  作者：Manman Wang、Guolan Dou、Daqing Shi

  DOI：10.1021/cc100062e

  日期：2010.7.12

  An efficient, convenient, one-pot synthesis of 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one and 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione was accomplished in good yields via the novel reductive cyclization of 2-nitrobenzamides with haloketones or keto acids mediated by SnCl2·2H2O system. A variety of substrates can participate in the process with good yields, making this methodology

  2,3,3a，4-四氢吡咯并[1,2 - a ]喹唑啉-5（1 H）-one和2,3,3a，4-四氢吡咯并[1,2-通过由SnCl 2 ·2H 2 O系统介导的2-硝基苯甲酰胺与卤代酮或酮酸的新型还原性环化反应，可以成功地制得]]喹唑啉-1,5-二酮。多种底物可以高收率参与该过程，从而使该方法适用于药物发现工作中的文库合成。
• New conditions for synthesis of (±)-2-monosubstituted and (±)-2,2-disubstituted 2,3-dihydro-4(1H)-quinazolinones from 2-nitro- and 2-aminobenzamide
  作者：Richard A. Bunce、Baskar Nammalwar

  DOI：10.1002/jhet.672

  日期：2011.9

  An efficient synthesis of (±)‐2‐monosubstituted and (±)‐2,2‐disubstituted 2,3‐dihydro‐4(1H)‐quinazolinones has been developed using a dissolving metal reduction‐condensative cyclization strategy. Treatment of 2‐nitrobenzamide and an aldehyde or ketone with iron powder in refluxing acetic acid affords high yields of the title compounds. More complex ring systems are available by incorporating additional

  使用溶解性金属还原-缩合环化策略开发了一种有效合成（±）-2-单取代和（±）-2,2-二取代的2,3-二氢-4（1 H）-喹唑啉酮的方法。用铁粉在回流的乙酸中处理2-硝基苯甲酰胺和醛或酮，可高收率得到标题化合物。通过将额外的反应性官能团γ引入醛或酮底物的羰基中，可以获得更复杂的环系统。介绍了该过程的范围和局限性以及优化的程序细节。通过使2-氨基苯甲酰胺与乙醛和酮在回流的乙酸中反应也可以访问相同的目标分子。J.杂环化​​学。（2011）。
• An efficient synthesis of pyrrolo[1,2-a]quinazolin-5(1H)-one derivatives with the aid of low-valent titanium reagent
  作者：Xuan Zhao、Da-Qing Shi

  DOI：10.1002/jhet.637

  日期：2011.5

  A short and facile synthesis of 2,3,3a,4‐tetrahydropyrrolo[1,2‐a]quinazolin‐5(1H)‐ones and 2,3,3a,4‐tetrahydropyrrolo[1,2‐a]quinazoline‐1,5‐diones in good yields via the novel reductive cyclization of 2‐nitrobenzamides with haloketones or 4‐oxopentanoic acid promoted by low‐valent titanium reagent is described. J. Heterocyclic Chem., (2011).

  甲基-2,3,3a，4-四氢吡咯并[1,2-的简短和简便合成一个]喹唑啉-5（1 ħ） -酮和甲基-2,3,3a，4-四氢吡咯并[1,2一]喹唑啉描述了通过低价钛试剂促进的2-硝基苯甲酰胺与卤代酮或4-氧代戊酸的新型还原环化，可实现高产率的1,5-二酮。J.杂环化​​学。（2011）。
• A facile heterogeneous catalytic approach for one-pot synthesis of fused benzoxazinones using Cuβ zeolite and Evaluation of biological activities
  作者：Suchitha Dasu、Krishna Sai Gajula、Vasu Amrutham、Murali Boosa、Ramulamma Madasu、Madhuri Lekkala、Sai Balaji Andugulapati、Narender Nama

  DOI：10.1016/j.tet.2024.133931

  日期：2024.4

  A simple heterogeneous catalytic process has been established for the single-step synthesis of fused benzoxazinones, quinazolinones, and thiadazines through Markownikoff's hydroamination followed by intramolecular cyclization using Cuβ zeolite. The probability and limitations of this catalytic approach were explored using various substrates. The efficiency and feasibility of scaling up the current

  建立了一种简单的多相催化工艺，通过马氏氢胺化，然后使用 Cuβ 沸石进行分子内环化，一步合成稠合苯并恶嗪酮、喹唑啉酮和噻嗪酮。使用各种底物探索了这种催化方法的可能性和局限性。通过克级实验证明了扩大当前催化系统的效率和可行性。此外，该催化剂可重复使用多达五个循环，其催化效率没有明显下降。此外，对合成的化合物进行了评估，以确定其作为抗人宫颈上皮样癌（HeLa）、小鼠乳腺癌（4T-1）和人肺腺癌（A-549）细胞系的抗癌剂的潜力。细胞毒性研究表明，该化合物对乳腺癌、宫颈癌和肺癌细胞具有抗癌活性。此外，还评估了它们对细菌和酵母的抗菌活性。该化合物表现出优异的抗真菌活性