ethyl 2-methyl-4-(4-hydroxyphenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate | 1353741-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: ethyl 2-methyl-4-(4-hydroxyphenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate
• 英文别名: ethyl 4-(4-hydroxyphenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate；ethyl 4-(4-hydroxyphenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate
• CAS: 1353741-23-7
• 化学式: C₂₀H₁₈N₂O₃S
• 分子量: 366.441
• InChiKey: FZCBKGWRPQYFJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻碘溴苯 、 5-ethoxycarbonyl-6-methyl-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione 在 bis-triphenylphosphine-palladium(II) chloride 、 丙戊酸 、 potassium carbonate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40 %的产率得到ethyl 2-methyl-4-(4-hydroxyphenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate
  参考文献：
  名称：

  Pd-catalyzed regioselective tandem C-S/C-N bond formation for modular synthesis of pyrimidine-fused benzothiazoles from o-dihaloarenes and 3,4-dihydropyrimidin-2-thiones

  摘要：

  A Pd-catalyzed annulation reaction for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via regioselective tandem C-S/C-N bond formation was developed. With PdCl2(PPh3)2 as the precatalyst, Davephos as the ligand, and K2CO3 as the base, various 3,4-dihydropyrimidin-2-thiones with o-dihaloarenes proceeded smoothly, and the desired products were obtained in moderate to good yields

  DOI：

  10.1055/a-2311-3930

文献信息

• Efficient and facile synthesis of heterocycles and their mechanistic consideration using kaolin
  作者：Pramod Kumar Sahu、Praveen Kumar Sahu、Dau Dayal Agarwal

  DOI：10.1039/c3ra40993g

  日期：——

  catalyzed solvent-free synthesis for new heterocyclic compounds is described. A series of heterocyclic compounds can be readily obtained using the three-component reaction of diketones, aldehydes and 2-amino benzothiazole, urea or thiourea. The mechanism of the three component kaolin catalyzed Biginelli (using urea and thiourea) and Biginelli like (using 2-amino benzothiazole) reaction has been investigated

  描述了用于新的杂环化合物的高岭土催化的无溶剂合成。使用二酮，醛和三酮的三组分反应可以轻松获得一系列杂环化合物2-氨基苯并噻唑， 尿素 或者 硫脲。三组分高岭土催化Biginelli的机理（使用尿素 和 硫脲）和Biginelli喜欢（使用 2-氨基苯并噻唑）反应已被调查。这是我们首次使用1 H NMR，13 C NMR和ESI-质谱表征来分离和表征关键中间体。机理研究强烈建议使用亚胺3和Knoevenagel型中间体4作为关键中间体。该反应简单，清洁并且在数分钟内获得了良好的产率。
• Nano-Co-[4-chlorophenyl-salicylaldimine-pyranopyrimidine dione]Cl2 as a new Schiff base complex and catalyst for the one-pot synthesis of some 4H-pyrimido[2,1-b]benzazoles
  作者：Ahmad Reza Moosavi-Zare、Hamid Goudarziafshar、Parva Fashi

  DOI：10.1007/s11164-020-04279-5

  日期：2020.12

  was prepared and fully characterized as a new nano-Schiff base complex. Nano-[Co-4CSP]Cl2 was successfully used as an efficient catalyst for the synthesis of some 4H-pyrimido[2,1-b]benzazoles such as 4H-pyrimido[2,1-b]benzothiazoles and 4H-pyrimido[2,1-b]benzimidazoles.

  Nano-Co-[4-clolorophenyl-salsylaldimine-pyranopyrimidine dione]Cl2 Nano-[Co-4CSP]Cl2} 被制备并充分表征为一种新的纳米席夫碱配合物。Nano-[Co-4CSP]Cl2 被成功用作合成一些 4H-嘧啶并[2,1-b]苯并唑类的高效催化剂，例如 4H-嘧啶并[2,1-b]苯并噻唑和 4H-嘧啶并[2 ,1-b]苯并咪唑。
• POM analyses and evaluation of in vitro antimicrobial, antitumor activity of 4H-pyrimido[2,1-b]benzothiazole derivatives
  作者：Pramod K. Sahu、Praveen K. Sahu、Pushkal Samadhiya、Puran L. Sahu、Dau D. Agarwal

  DOI：10.1007/s00044-016-1589-8

  日期：2016.8

  facile, efficient, and convenient synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives is described using aromatic aldehydes, ethyl acetoacetate, and 2-amino benzothiazole in the presence of l-proline under solvent-free conditions. Present methodology has advantages such as short reaction time, no side products, and easy to work up. Synthesized library compounds have been evaluated for their antitumor

  摘要一种简便，高效和4的简便合成ħ嘧啶并[2,1- b ]苯并噻唑衍生物是使用芳族醛描述，乙酰乙酸乙酯，和2-氨基苯并噻唑在存在升-脯氨酸在无溶剂的条件下。当前的方法具有诸如反应时间短，无副产物和易于加工的优点。已经评估了合成的文库化合物的抗肿瘤和抗微生物活性。此外，我们已经使用分子特性分析将实验工作与理论参数进行了比较，以开发出有关制备嘧啶基苯并噻唑衍生物的新思路，以用于其可能用于治疗癌症和慢性微生物疾病。结论是，Petra / osiris / molinspiration（POM）分析可能被证明是关联4 H -pyrimido [2,1- b]结构特征的合适方法。]苯并噻唑衍生物具有令人满意的抗微生物/抗肿瘤活性，可能有助于开发新型抗药性药物。 图形概要
• Nano-cellulose/BF3/Fe3O4: a magnetic bio-based nano-catalyst for the synthesis of pyrimido[2,1-b]benzothiazoles under solvent-free conditions
  作者：Bi Bi Fatemeh Mirjalili、Fatemeh Aref

  DOI：10.1007/s11164-018-3401-5

  日期：2018.7

  Nano-cellulose/BF3/Fe3O4 is a bio-based and eco-friendly catalyst with high catalytic activity. Easy separation with an external magnet and recyclability without significant loss of its activity are some advantages of this catalyst. Nano-cellulose/BF3/Fe3O4 was characterized by Fourier transform infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy, X-ray diffraction, X-ray fluorescence, vibrating sample magnetometry, thermogravimetric analysis, and BET theory. The catalyst was applied for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via one-pot condensation of aldehydes, 2-aminobenzothiazol and ethyl acetoacetate, under solvent-free conditions at 100 °C. This method offers several advantages including easy work-up, excellent yields and short reaction time.

  纳米纤维素/BF3/Fe3O4 是一种生物基环保催化剂，具有很高的催化活性。这种催化剂的一些优点是易于用外部磁铁分离，而且可回收利用，其活性不会明显降低。傅立叶变换红外光谱、场发射扫描电子显微镜、透射电子显微镜、X 射线衍射、X 射线荧光、振动样品磁力计、热重分析和 BET 理论对纳米纤维素/BF3/Fe3O4 进行了表征。催化剂被用于在 100 ℃ 无溶剂条件下，通过醛、2-氨基苯并噻唑和乙酰乙酸乙酯的一锅缩合合成 4H-嘧啶并[2,1-b]苯并噻唑衍生物。该方法具有操作简便、产率高和反应时间短等优点。
• Effect of substituent dependent molecular structure on anti-corrosive behavior of one-pot multicomponent synthesized pyrimido [2,1-B] benzothiazoles: Computer modelling supported experimental studies
  作者：Chandrabhan Verma、M.A. Quraishi、I.B. Obot、Eno E. Ebenso

  DOI：10.1016/j.molliq.2019.110972

  日期：2019.8

  dependent molecular structures on inhibition property of four heterocyclic compounds containing nitrogen, sulfur and oxygen atoms for mild steel corrosion in 1 M HCl. Their inhibition effect was measured using weight loss, open circuit potential (OCP), potentiodynamic polarization (PDP) and electrochemical impedance spectroscopy (EIS), scanning electron microscopy (SEM) and atomic force microscopy (AFM) and

  本研究旨在证明取代基依赖性分子结构对四种含氮，硫和氧原子的杂环化合物在1 M HCl中对轻度钢腐蚀的抑制性能。使用重量损失，开路电势（OCP），电势极化（PDP）和电化学阻抗谱（EIS），扫描电子显微镜（SEM）和原子力显微镜（AFM）和计算方法来测量它们的抑制作用。实验和计算研究的结果表明，它们的抑制效率遵循以下顺序：PBT-IV（–OCH 3  + –OH）> PBT-III（–OH）> PBT-II（–CH 3）> PBT-I（–H）。在测试的化合物中，PBT-IV是最佳的腐蚀抑制剂，在42.8×10 -5  M的浓度下显示最高的抑制效率为94.88％。酸性介质中PBT的存在会导致R ct值增加，电流密度（i corr）值减小。DFT结果表明，电子释放取代基（-OCH 3，-OH和-CH 3）的存在增强了负责金属表面抑制剂相互作用的前沿分子轨道上的电子密度。被研究化合物的分子结构具有高电子给予能力（高E