7H-benzo[h]pyrido[2,1-b]quinazolin-7-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 7H-benzo[h]pyrido[2,1-b]quinazolin-7-one
• 英文别名: 12,18-Diazatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2,4,6,8,13,15,17-octaen-11-one；12,18-diazatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2,4,6,8,13,15,17-octaen-11-one
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: JEHGBTHNHGIRFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-vinylnaphthalen-1-yl)pyridin-2-amine 在 水 、 碘 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以81%的产率得到7H-benzo[h]pyrido[2,1-b]quinazolin-7-one
  参考文献：
  名称：

  碘介导的 C=C 双键裂解对吡啶并[2,1-b]喹唑啉酮

  摘要：

  描述了使用分子碘的不含过渡金属的 C=C 双键断裂反应。在作为碱基的 K 2 CO 3存在下，I 2介导的 C=C 键断裂，随后N -(2-乙烯基芳基)吡啶-2-胺底物的分子内环化产生吡啶并[2,1- b ]喹唑啉酮和相关杂环化合物。该反应可以在克级上完成，并已成功应用于合成具有重要生物学特性的化合物，包括外排泵抑制和抗过敏活性。

  DOI：

  10.1021/acs.orglett.2c01183

文献信息

• Palladium‐Catalyzed Carbonylative Cyclization of Arenes by CH Bond Activation with DMF as the Carbonyl Source
  作者：Jianbin Chen、Jian‐Bo Feng、Kishore Natte、Xiao‐Feng Wu

  DOI：10.1002/chem.201503314

  日期：2015.11.9

  autoclave‐free protocol for the synthesis of 11H‐pyrido[2,1‐b]quinazolin‐11‐ones has been developed. Quinazolinones, which are omnipresent motif in many pharmaceuticals and agrochemicals, were prepared in good yields by CH bond activation and annulation using DMF as the CO surrogate. A 13CO‐labelled DMF control experiment demonstrated that CO gas was released from the carbonyl of DMF with acid as

  为11的合成一种新型的钯催化CO-气体和无高压釜协议ħ -吡啶并[2,1- b ]喹唑啉-11-那些已经研制成功。喹唑啉酮是许多药物和农用化学品中无处不在的基序，它是通过CH键活化和使用DMF作为CO替代物进行环化而制备的，产率很高。一项13 CO标记的DMF对照实验表明，以酸为促进剂从DMF的羰基中释放出CO气体。的动力学同位素效应（KIE）值指示，在C  ħ活化步骤可以不是在速率决定步骤有关。该方法操作简单，显示了广泛的底物范围，具有良好至极好的产率。
• Buchwald-Hartwig Amination of β-Chloroacroleins by Lactams and Heteroarylamines
  作者：Stéphanie Hesse、Gilbert Kirsch

  DOI：10.1055/s-2007-966034

  日期：——

  β-Chloroacroleins reacted readily with lactams and several heteroarylamines (aminopyridines, aminoquinoline and azoles) under standard Buchwald-Hartwig amination conditions. Both Pd(OAc)2/Binap or Pd(OAc)2/Xantphos were efficient catalytic systems in the presence of Cs2CO3 as base.

  在标准布赫瓦尔德-哈特维格胺化条件下，δ-氯丙烯醛很容易与内酰胺和几种杂芳基胺（氨基吡啶、氨基喹啉和偶氮唑）发生反应。在以 Cs2CO3 为碱的情况下，Pd(OAc)2/Binap 或 Pd(OAc)2/Xantphos 都是高效的催化系统。
• Pd/C-catalyzed carbonylative C–H activation with DMF as the CO source
  作者：Jianbin Chen、Kishore Natte、Xiao-Feng Wu

  DOI：10.1016/j.tetlet.2015.09.142

  日期：2015.11

  An interesting Pd/C-catalyzed carbonylative cyclization of N-arylpyridin-2-amine derivatives via C-H activation has been developed. With DMF as the CO source, the desired quinazolinones were formed in moderate to good yields with good functional group tolerance. (C) 2015 Elsevier Ltd. All rights reserved.
• A novel approach for the one-pot synthesis of linear and angular fused quinazolinones
  作者：Arindam Maity、Shyamal Mondal、Rupankar Paira、Abhijit Hazra、Subhendu Naskar、Krishnendu B. Sahu、Pritam Saha、Sukdeb Banerjee、Nirup B. Mondal

  DOI：10.1016/j.tetlet.2011.04.019

  日期：2011.6

  A convenient and inexpensive one step methodology has been developed for the synthesis of linear and angular fused quinazolinones. The protocol, which uses amino heterocycles and o-bromo benzyl/naphthyl bromides as reactants, Cut as catalyst, Cs2CO3 as base, L-proline as ligand, and DMF as solvent, proceeds via nucleophilic aromatic substitution of the N-heteroaromatic cationic intermediate followed by in situ aerial oxidation at the benzylic position to the quinazolinone scaffold. (C) 2011 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Aerobic Oxidative Annulation and Carbon-Carbon Bond Cleavage of Arylacetamides: Domino Synthesis of Fused Quinazolinones
  作者：Jie Sun、Qitao Tan、Wusong Yang、Bingxin Liu、Bin Xu

  DOI：10.1002/adsc.201300818

  日期：2014.2.10

  AbstractAn efficient copper‐catalyzed tandem aerobic oxidative annulation and carbon‐carbon bond cleavage reaction was developed from easily accessible arylacetamides, which provides a direct approach for the domino synthesis of a vast array of tricyclic or tetracyclic fused quinazolinone alkaloid structures. A plausible reaction mechanism is proposed involving an aerobic benzylic oxidation/cyclization/decarbonylation cascade.magnified image