3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one | 25816-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one
• 英文别名: 3-phenyl-pyrido[1,2-a]pyrimidin-4-one；3-Phenyl-4H-pyrido<1,2-a>pyrimidin-4-on；3-Phenylpyrido[1,2-a]pyrimidin-4-one
• CAS: 25816-51-7
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: CWYAONMNVJBSAX-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  396.9±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  2-氨基吡啶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one
  参考文献：
  名称：

  Convenient Synthesis of Novel Phenylpyrimido[1,2-c]thienopyrimidinones as IL-6/STAT3 Inhibitors

  摘要：

  New phenylpyrimido[1,2-c]thienopyrimidinones 4A and 4B were easily prepared in good yields by the one-pot reaction of formamidine derivatives 2 of 4-aminothienopyrimidine 1 with phenylacetyl chlorides. The application of this convenient and reliable method could be used for the synthesis of a variety of pyrimido[1,2-c]thienopyrimidinone derivatives of biological importance. Some of the compounds synthesized showed strong IL-6/STAT3 inhibition.

  DOI：

  10.3987/com-15-13166

文献信息

• Suzuki–Miyaura cross-coupling reactions of halo derivatives of 4H-pyrido[1,2-a]pyrimidin-4-ones
  作者：Annamária Molnár、Anita Kapros、László Párkányi、Zoltán Mucsi、Gábor Vlád、István Hermecz

  DOI：10.1039/c1ob05505d

  日期：——

  cross-coupling reactions of halo derivatives of 4H-pyrido[1,2-a]pyrimidin-4-one with (het)arylboronic acids allow easy access to (het)aryl and vinyl derivatives of this bicycle in good to excellent yields, even from chloro derivatives. The sequence of reactivity of the halogen in the different positions of the ring system was also investigated. 6-Phenyl-4H-pyrido[1,2-a]pyrimidin-4-one could be prepared by thermal

  钯催化的卤素衍生物的Suzuki-Miyaura交叉偶联反应 4 H-吡啶并[1,2- a ]嘧啶-4-一与（杂）芳基硼酸一起使用，即使从氯代衍生物中也可以很容易地获得该自行车的（杂）芳基和乙烯基衍生物。还研究了卤素在环系统不同位置的反应顺序。6-苯基-4 H-吡啶并[1,2- a ]嘧啶-4-一 可以通过热环化制备 异亚丙基（6-苯基吡啶-2-基氨基）亚甲基丙二酸酯，以及少量的7-苯基-1,4-二氢-1,8-萘啶-4-酮。
• Catalytic Photoredox C–H Arylation of 4-Oxo-4<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts
  作者：Kris Antolinc、Helena Brodnik、Uroš Grošelj、Bogdan Štefane、Nejc Petek、Jurij Svete

  DOI：10.1021/acs.joc.3c01517

  日期：2023.10.6

  presence of eosin Y disodium salt (EY-Na2) as a photocatalyst furnished the corresponding arylation products in 8–63% yields. The proposed photocatalytic cycle is analogous to that proposed previously for closely related photoredox C–H arylations with aryl diazonium salts as aryl radical sources. This method has a broad substrate scope and represents a metal-free alternative for the synthesis of 3-heteroaryl-substituted

  在曙红 Y 二钠盐 ( EY-Na 2 ) 作为光催化剂的情况下，用绿光 (510 nm) 照射标题重氮盐和杂芳烃的混合物，得到相应的芳基化产物，产率为 8-63%。所提出的光催化循环类似于之前提出的以芳基重氮盐作为芳基自由基源的密切相关的光氧化还原C-H芳基化反应。该方法具有广泛的底物范围，是合成具有桥头氮原子的 3-杂芳基取代的 4 H-喹嗪-4-酮以及叠氮基和偶氮基稠合嘧啶酮的无金属替代方案。
• Pd-Catalyzed Ag(I)-Promoted C3-Arylation of Pyrido[1,2-<i>a</i>]pyrimidin-4-ones with Bromo/Iodo-Arenes
  作者：Sankar K. Guchhait、Garima Priyadarshani

  DOI：10.1021/acs.joc.5b01573

  日期：2015.8.21

  A regioselective Ag(I)-promoted Pd-catalyzed C3-H activation arylation of pyrido[1,2-a]pyrimidin-4-ones with bromo/iodo-(hetero)arenes under aqueous conditions has been developed. It affords an efficient access to pharmaceutically important versatile 3-arylpyrido[1,2-a]pyrimidin-4-ones. Interestingly, the arylation undergoes via a pathway with an unusual feature involving the formation of cationic arylpalladium species promoted by halo-sequestering Ag salts enabling concerted C3-palladation-deprotonation, as explored by relevant experiments and spectroscopic studies. The present approach is step economical, good yielding, and compatible with various functionalities and applicable to a wide range of starting materials.
• Scaffold-hopping of bioactive flavonoids: Discovery of aryl-pyridopyrimidinones as potent anticancer agents that inhibit catalytic role of topoisomerase IIα
  作者：Garima Priyadarshani、Suyog Amrutkar、Anmada Nayak、Uttam C. Banerjee、Chanakya N. Kundu、Sankar K. Guchhait

  DOI：10.1016/j.ejmech.2016.06.024

  日期：2016.10

  A strategy of scaffold-hopping of bioactive natural products, flavones and isofl avones, leading to target-based discovery of potent anticancer agents has been reported for the first time. Scaffold-hopped flavones, 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones and the scaffold-hopped isofiavones, 3-aryl-pyrido[1,2-a]pyrimidin-4-ones were synthesized via Pd-catalyzed activation-arylation methods. Most of the compounds were found to exhibit pronounced human topoisomerase II alpha (hTopoll alpha) inhibitory activities and several compounds were found to be more potent than etoposide (a hTopoll alpha-inhibiting anticancer drug). These classes of compounds were found to be hTopoll alpha-selective catalytic inhibitors while not interfering with topoisomerase I and interacted with DNA plausibly in groove domain. Cytotoxicities against various cancer cells, low toxicity in normal cells, and apoptotic effects were observed. Interestingly, compared to parent flavones/isoflavones, their scaffold-hopped analogs bearing alike functionalities showed significant/enhanced hTopoII alpha-inhibitory and cytotoxic properties, indicating the importance of a natural product-based scaffold-hopping strategy in the drug discovery. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Convenient Synthesis of Novel Phenylpyrimido[1,2-c]thienopyrimidinones as IL-6/STAT3 Inhibitors
  作者：Yang-Heon Song、Jae Hoo Park、So Young Hong、Jungah Kim、Hyuck Joo Lee、Hyun Ho Lee、Ka Young Kim、Seung Woong Lee、Hyun-Mee Oh、Mun-Chul Rho、Beom-Gyu Lee

  DOI：10.3987/com-15-13166

  日期：——

  New phenylpyrimido[1,2-c]thienopyrimidinones 4A and 4B were easily prepared in good yields by the one-pot reaction of formamidine derivatives 2 of 4-aminothienopyrimidine 1 with phenylacetyl chlorides. The application of this convenient and reliable method could be used for the synthesis of a variety of pyrimido[1,2-c]thienopyrimidinone derivatives of biological importance. Some of the compounds synthesized showed strong IL-6/STAT3 inhibition.