ethyl 4-(2-methoxyphenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate

• 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 4-(2-methoxyphenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate
• 英文别名: ethyl 4-(2-methoxyphenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate
• 化学式: C₂₁H₂₀N₂O₃S
• 分子量: 380.467
• InChiKey: MVVCVZLHCQRBFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻碘溴苯 、 5-ethoxycarbonyl-4-(2-methoxyphenyl)-6-methyl-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46 %的产率得到ethyl 4-(2-methoxyphenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-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

• A Simple Approach to the One-Pot Three Component Synthesis of 4Hpyrimido [2,1-b] benzothiazole Derivatives Using Polyethylene Glycol (PEG-400)
  作者：Prabhakar Rairala、Bandi Yadagiri、Rajashaker Bantu、Vijayacharan Guguloth、Lingaiah Nagarapu

  DOI：10.2174/1570178612666150113231342

  日期：2015.3.3

  PEG-400 was found to be an inexpensive, non-toxic and eco-friendly reaction medium for synthesis of pyramido[2,1-b]benzothiazole derivatives. Utilizing this protocol, we are capable of various pyrimido[2,1-b]benzothiazole derivatives 4a-k and 6a-d were synthesised. The reaction between aminobenzothiazole 1, aromatic aldehydes 2a-k and ethyl acetoacetate 3/ diethyl malonate 5 at room temperature for 1-2 h furnished required compounds with good to excellent yields (85-93%). Here we observed carboxylic acid compounds instead of ester compounds when diethyl malonate was used as the substrate, whereas ethyl acetoacetate showed no signs. The reactions are easy to perform, atom-economic, require less reaction time and allow generation of the biologically potent pyrimido[2,1-b]benzothiazole frameworks from readily accessible starting materials.

  研究发现，PEG-400 是合成嘧啶并[2,1-b]苯并噻唑衍生物的一种廉价、无毒且环保的反应介质。利用这一方案，我们能够合成各种嘧啶并[2,1-b]苯并噻唑衍生物 4a-k 和 6a-d。氨基苯并噻唑 1、芳香醛 2a-k 和乙酰乙酸乙酯 3/ 丙二酸二乙酯 5 在室温下反应 1-2 小时后，生成了所需的化合物，收率高达 85-93%。在这里，当丙二酸二乙酯作为底物时，我们观察到的是羧酸化合物而不是酯类化合物，而乙酰乙酸乙酯则没有任何迹象。这些反应易于进行、原子经济、所需反应时间较短，并能从容易获得的起始材料中生成具有生物活性的嘧啶并[2,1-b]苯并噻唑框架。
• 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
  作者：xuying hu、ruiqi Liu、shiwen Fu、Lianxu Shi、Chunxia Chen、Jinsong Peng

  DOI：10.1055/a-2311-3930

  日期：——

  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