quinazolin-4(3H)-one-2-d

• 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: quinazolin-4(3H)-one-2-d
• 英文别名: 2-deuterio-3H-quinazolin-4-one
• 化学式: C₈H₆N₂O
• 分子量: 147.141
• InChiKey: QMNUDYFKZYBWQX-UICOGKGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基苯甲腈 在 cobalt(II) nitrate hexahydrate 、 三[2-(二苯基磷)乙基]磷 、 水 、 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.5h， 生成 quinazolin-4(3H)-one-2-d
  参考文献：
  名称：

  Cobalt-Catalyzed Tandem Transformation of 2-Aminobenzonitriles to Quinazolinones Using Hydration and Dehydrogenative Coupling Strategy

  摘要：

  A tandem synthesis of quinazolinones from 2-aminobenzonitriles is demonstrated here by using an aliphatic alcohol-water system. For this transformation, a cheap and easily available cobalt salt and P(CH2CH2PPh2)(3)(PP3) ligand were employed. The substrate scope, scalability, and synthesis of natural products exhibited the vitality of this protocol.

  DOI：

  10.1021/acs.joc.0c01307

文献信息

• Late-Stage C–H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines
  作者：Álvaro Gutiérrez-Bonet、Camille Remeur、Jennifer K. Matsui、Gary A. Molander

  DOI：10.1021/jacs.7b05899

  日期：2017.9.6

  heterocyclic bases and 1,4-quinones. DHPs are readily prepared from aldehydes, and considering that aldehydes normally require harsh reaction conditions to take part in such transformations, with mixtures of alkylated and acylated products often being obtained, this net decarbonylative alkylation approach becomes particularly useful. The present method takes place under mild reaction conditions and requires

  在氧化条件下，1,4-二氢吡啶 (DHP) 发生均裂，仅形成以 Csp3 为中心的自由基，该自由基可以参与杂环碱基和 1,4-醌的 CH 烷基化。DHP很容易由醛制备，并且考虑到醛通常需要苛刻的反应条件来参与这种转化，并且经常获得烷基化和酰化产物的混合物，这种净脱羰烷基化方法变得特别有用。本方法在温和的反应条件下进行，仅需要过硫酸盐作为化学计量氧化剂，使得该方法适合复杂分子的后期CH烷基化。值得注意的是，结构复杂的药剂可以用该方案功能化或制备，例如抗疟药 Atovaquone 和抗疟药 Parvaquone，从而证明其适用性。机理研究揭示了可能通过形成脱芳构中间体的自由基链过程，从而更深入地了解控制这些自由基前体反应性的因素。
• Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon
  作者：Seohoo Lee、Jaeuk Sim、Hyeju Jo、Mayavan Viji、Lanka Srinu、Kiho Lee、Heesoon Lee、Vishwanath Manjunatha、Jae-Kyung Jung

  DOI：10.1039/c9ob01629e

  日期：——

  Biologically important quinazolinones have been synthesized from 2-aminobenzamides and DMSO. The key feature of the reaction is the utilization of DMSO as a methine source for intramolecular oxidative annulation. The CNS depressant drug methaqualone has also been synthesized by our methodology. The present method involves the synthesis of quinazolinones with a broad substrate scope and a good yield

  从2-氨基苯甲酰胺和DMSO合成了生物学上重要的喹唑啉酮。该反应的关键特征是利用DMSO作为次甲基源用于分子内氧化环化。我们的方法还合成了CNS抑制剂药物甲喹酮。本方法涉及具有宽底物范围和良好收率的喹唑啉酮的合成。
• Visible-light induced copper(<scp>i</scp>)-catalyzed oxidative cyclization of <i>o</i>-aminobenzamides with methanol and ethanol <i>via</i> HAT
  作者：Mandapati Bhargava Reddy、Kesavan Prasanth、Ramasamy Anandhan

  DOI：10.1039/d0ob02234a

  日期：——

  The activation of the C(sp³)–H of MeOH via HAT for the synthesis of quinazolinones has been achieved using an in situ generated ligand–copper-superoxo complex under visible light.

  通过HAT直接激活甲醇的C(sp³)–H键，利用现场生成的配体–铜超氧化物复合物在可见光下成功合成喹唑啉酮。
• Uncatalyzed microwave deuterium exchange labeling of bleomycin A2
  作者：Steve A. de Keczer、Tim S. Lane、Mohammad R. Masjedizadeh

  DOI：10.1002/jlcr.857

  日期：2004.10.15

  Bleomycin sulfate in D2O was deuterated using microwave irradiation under catalyst free conditions. Following the removal of labile deuterium and purification, bleomycin A2 with mass M + 1 to M + 7 was obtained. Successful selective uncatalyzed microwave deuterium exchange reactions on examples from the following classes of heterocycles are also described: imidazole, thiazole, indole, purine, and quinazoline. The described method was used as a test for non-labile active protons. Copyright © 2004 John Wiley & Sons, Ltd.

  在无催化剂条件下，使用微波辐照对 D2O 中的博莱霉素进行氚化。在去除可变氘并纯化后，得到了质量为 M + 1 至 M + 7 的博莱霉素 A2。此外，还介绍了以下几类杂环的成功选择性非催化微波氘交换反应：咪唑、噻唑、吲哚、嘌呤和喹唑啉。所描述的方法可用于测试非易腐活性质子。Copyright © 2004 John Wiley & Sons, Ltd. All Rights Reserved.
• Cu-Catalyzed Carbocyclization for General Synthesis of <i>N</i>-Containing Heterocyclics Enabled by BrCF₂COOEt as a C1 Source
  作者：Xiao-Fang Song、Li-Jing Zhang、Xing-Guo Zhang、Hai-Yong Tu

  DOI：10.1021/acs.joc.3c02827

  日期：2024.3.1

  bromodifluoroacetate has been developed. Ethyl bromodifluoroacetate is employed as the C1 source via quadruple cleavage in this transformation. This reaction can afford a variety of N-containing heterocyclics with satisfactory yields and excellent functional group compatibility.

  已经开发出一种实用且高效的铜催化 2-官能化苯胺与溴二氟乙酸乙酯的碳环化反应。在此转化中，溴二氟乙酸乙酯通过四次裂解用作 C1 源。该反应可以得到多种含氮杂环化合物，且产率令人满意，官能团相容性优异。