2-methyl-4-(2-chlorophenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylic acid ethyl ester

• 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: 2-methyl-4-(2-chlorophenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-(2-chlorophenyl)-2-methyl-4H-benzo[4,5][1,3]thiazolo[3,2-a]pyrimidine-3-carboxylate；ethyl 2-methyl-4-(2-chlorophenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate；ethyl 4-(2-chlorophenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate；Ethyl 4-(2-chlorophenyl)-2-methyl-4h-benzo[4,5][1,3]thiazolo[3,2-a]-pyrimidine-3-carboxylate
• 化学式: C₂₀H₁₇ClN₂O₂S
• 分子量: 384.886
• InChiKey: ZTLCGVVMSMFOSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻碘溴苯 、 4-(2-氯苯基)-1,2,3,4-四氢-6-甲基-2-硫代-5-嘧啶羧酸乙酯 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23 %的产率得到2-methyl-4-(2-chlorophenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylic acid ethyl ester
  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

• 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/ / 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。
• Nano-kaolin/Ti⁴⁺/Fe₃O₄: a magnetic reusable nano-catalyst for the synthesis of pyrimido[2,1-<i>b</i>]benzothiazoles
  作者：Bi Bi Fatemeh Mirjalili、Roya Soltani

  DOI：10.1039/c9ra01767d

  日期：——

  nano-catalyst was synthesized, and its structural properties were characterized using various techniques such as Fourier transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), a vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA) and energy-dispersive X-ray spectroscopy (EDX). This catalyst

  本文合成了一种新型磁性纳米催化剂纳米高岭土/Ti 4+ /Fe 3 O 4 ，并采用傅里叶变换红外（FTIR）光谱、场发射扫描电子显微镜（FE）等多种技术对其结构性质进行了表征。 -SEM)、透射电子显微镜 (TEM)、X 射线衍射 (XRD)、振动样品磁力计 (VSM)、热重分析 (TGA) 和能量色散 X 射线光谱 (EDX)。该催化剂用于合成嘧啶并[2,1- b ]苯并噻唑2-氨基苯并噻唑、醛和 β-酮酯在 100 °C 无溶剂条件下的一锅缩合反应。这种简单的协议具有许多优点，例如易于处理、产品收率高、反应时间短和催化剂的可重复使用性。
• Fe₃O₄@nano-cellulose/TiCl: a bio-based and magnetically recoverable nano-catalyst for the synthesis of pyrimido[2,1-b]benzothiazole derivatives
  作者：Sara Azad、Bi Bi Fatameh Mirjalili

  DOI：10.1039/c6ra13566h

  日期：——

  nano-catalyst were studied with some different techniques such as Fourier transform infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FESEM), X-ray diffraction (XRD), X-ray fluorescence (XRF), vibrating sample magnetometry (VSM) and thermo-gravimetric analysis (TGA). The catalyst was found to be active for the synthesis of 4H-pyrimido[2,1-b]benzothiazoles via one-pot three-component

  磁性核-壳纳米粒子Fe 3 O 4 @纳米纤维素是通过在纳米纤维素水溶液中通过NH 4 OH原位共沉淀Fe 3+和Fe 2+离子而制备的。用四氯化钛处理Fe 3 O 4纳米纤维素导致Fe 3 O 4的形成纳米纤维素/ TiCl作为新型可回收催化剂。随后，使用诸如傅里叶变换红外（FT-IR）光谱，场发射扫描电子显微镜（FESEM），X射线衍射（XRD）等不同技术研究了制备的纳米催化剂的结构，形态和磁性。 ，X射线荧光（XRF），振动样品磁力分析（VSM）和热重分析（TGA）。发现该催化剂具有活性，可通过以下途径合成4 H-嘧啶并[2,1- b ]苯并噻唑乙醛，乙酰乙酸乙酯和2-氨基苯并噻唑在无溶剂条件下于70°C进行一锅三组分反应。该方法的优点是反应条件温和，后处理容易，产率高，反应时间短，催化剂的磁分离简单以及其可循环利用多达七个循环而没有明显损失效率的优点。
• Nano-TiCl2/cellulose: an eco-friendly bio-based catalyst for one-pot synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives
  作者：Sara Azad、Bi Bi Fatameh Mirjalili

  DOI：10.1007/s11164-016-2725-2

  日期：2017.3

  microscopy. Nano-TiCl2/cellulose has been shown to effectively promote multi-component synthesis of 4 H -pyrimido[2,1- b ]benzothiazole derivatives by reaction of aldehydes, β-ketoester, and 2-amino benzothiazole under thermal conditions in polyethylene glycol 400 as solvent. Simple methodology,an eco-friendly catalyst, a clean procedure, easy work-up, and excellent yields are some of the important advantages

  摘要 纤维素是最丰富的天然碳基生物聚合物，其包含具有亲核特性的自由OH基团，可键合至路易斯酸（如TiCl 4）。通过在室温条件下，以纳米纤维素与TiCl 4在二氯甲烷为溶剂中反应，制备了纳米-TiCl 2 /纤维素作为生物基环保型路易斯酸催化剂。该催化剂已通过傅里叶变换红外光谱，场发射扫描电子显微镜，粉末X射线衍射，能量色散X射线光谱，X射线荧光技术和透射电子显微镜表征。纳米TiCl 2 /纤维素已被证明可有效促进4的多组分合成 在热条件下，以聚乙二醇400为溶剂，通过醛，β-酮酸酯和2-氨基苯并噻唑的反应，生成 H- 嘧啶并[ 2,1- b ]苯并噻唑衍生物。简单的方法学，环保的催化剂，清洁的程序，容易的后处理以及优异的收率是该方案的一些重要优点。 图形概要
• Fe₃O₄@nano-cellulose/Cu(<scp>ii</scp>): a bio-based and magnetically recoverable nano-catalyst for the synthesis of 4<i>H</i>-pyrimido[2,1-<i>b</i>]benzothiazole derivatives
  作者：Nasrin Safajoo、Bi Bi Fatemah Mirjalili、Abdolhamid Bamoniri

  DOI：10.1039/c8ra09203f

  日期：——

  characterized by FT-IR, XRD, VSM, FESEM, TEM, XRF, EDS and TGA. In this research, the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives was developed via a three component reaction of aromatic aldehyde, 2-aminobenzothiazole and ethyl acetoacetate using Fe3O4@nano-cellulose/Cu(II) under solvent-free condition at 80 °C. Some advantages of this protocol are good yields, environmentally benign, easy work-up

  通过在纳米纤维素水悬浮液中原位共沉淀Fe 2+和Fe 3+离子，制备了Fe 3 O 4 @纳米纤维素/Cu( II )作为绿色生物基磁性催化剂。通过FT-IR、XRD、VSM、FESEM、TEM、XRF、EDS和TGA对上述磁性非均相催化剂进行了表征。本研究采用Fe 3 O 4 @纳米纤维素/ Cu ( II) 在 80 °C 无溶剂条件下。该协议的一些优点是产量高、环境友好、易于处理和催化剂的适度可重复使用性。产物结构经FT-IR、1 H NMR和13 C NMR光谱证实。