3,3-dimethyl-12-(4-methoxyphenyl)-2,3,4,12-tetrahydro-1H-benzo[4,5][1,3]thiazolo[2,3-b]quinazolin-1(2h)-one | 1413644-39-9

• 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: 3,3-dimethyl-12-(4-methoxyphenyl)-2,3,4,12-tetrahydro-1H-benzo[4,5][1,3]thiazolo[2,3-b]quinazolin-1(2h)-one
• 英文别名: 12-(4-methoxyphenyl)-3,3-dimethyl-2,3,4,12-tetrahydro-1H-benzo[4,5]thiazolo[2,3-b]quinazolin-1-one；12-(4-methoxyphenyl)-3,3-dimethyl-4,12-dihydro-2H-[1,3]benzothiazolo[2,3-b]quinazolin-1-one
• CAS: 1413644-39-9
• 化学式: C₂₃H₂₂N₂O₂S
• 分子量: 390.506
• InChiKey: GAHFTNBKNBEROD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-氨基苯并噻唑 、 4-甲氧基苯甲醛 、 5,5-二甲基-1,3-环己二酮 在 iron(III) trifluoride 作用下， 以 neat (no solvent) 为溶剂， 以95%的产率得到3,3-dimethyl-12-(4-methoxyphenyl)-2,3,4,12-tetrahydro-1H-benzo[4,5][1,3]thiazolo[2,3-b]quinazolin-1(2h)-one
  参考文献：
  名称：

  氟化铁：无溶剂条件下一锅合成4 H-嘧啶[2,1- b ]苯并噻唑的最有效催化剂

  摘要：

  描述了一种在无溶剂介质中制备4 H-嘧啶并[2,1- b ]苯并噻唑衍生物的新型氟化铁辅助方便高效策略。该反应可以在低催化剂负载下以优异的官能团耐受性进行。催化剂可以容易地回收并再用于至少三轮反应的下一步反应，而对产物的收率没有任何明显的影响。易于回收的催化剂和高收率的产品使该方案具有吸引力，可持续性和经济性。

  DOI：

  10.1016/j.tet.2014.05.094

文献信息

• Iron fluoride: the most efficient catalyst for one-pot synthesis of 4H-pyrimido[2,1-b]benzothiazoles under solvent-free conditions
  作者：Amol B. Atar、Yong Seok Jeong、Yeon Tae Jeong

  DOI：10.1016/j.tet.2014.05.094

  日期：2014.8

  A new iron fluoride assisted convenient and efficient strategy for the preparation of 4H-pyrimido[2,1-b]benzothiazoles derivatives in solvent-free media is described. The reactions can be performed at low-catalyst loadings with excellent functional group tolerance. The catalyst can be readily recovered and reused for next reaction for at least three runs without any significant impact on the yields

  描述了一种在无溶剂介质中制备4 H-嘧啶并[2,1- b ]苯并噻唑衍生物的新型氟化铁辅助方便高效策略。该反应可以在低催化剂负载下以优异的官能团耐受性进行。催化剂可以容易地回收并再用于至少三轮反应的下一步反应，而对产物的收率没有任何明显的影响。易于回收的催化剂和高收率的产品使该方案具有吸引力，可持续性和经济性。
• Green and highly efficient MCR strategy for the synthesis of pyrimidine analogs in water via C–C and C–N bond formation and docking studies
  作者：Ayushi Sethiya、Jay Soni、Anu Manhas、Prakash Chandra Jha、Shikha Agarwal

  DOI：10.1007/s11164-021-04529-0

  日期：2021.11

  protocol has many fascinating features, viz. high product yields, eco-friendly, milder reaction conditions, avoiding the use of hazardous solvent, and easily recoverable and reusable catalyst. The good functional group tolerance with a series of derivatives has been demonstrated. Molecular docking studies were performed on the synthesized compounds using Staphylococcus aureus dihydropteroate synthase (saDHPS)

  目前的研究涉及在硫胺素盐酸盐 (VB 1 ) 作为有机催化剂存在下，通过芳香醛、2-氨基苯并噻唑和二甲酮的反应合成一些新型嘧啶衍生物。使用 VB 1作为催化剂消除了产品中金属污染的危险，这对生态友好途径是可行的，并被证明是在可持续条件下更好的催化剂。反应机理包括 Knoevenagel 缩合，然后是 Michael 加成。设计的协议具有许多引人入胜的功能，即。产品收率高，环境友好，反应条件温和，避免使用有害溶剂，催化剂易于回收和重复使用。已经证明了一系列衍生物具有良好的官能团耐受性。使用金黄色葡萄球菌二氢蝶酸合酶(saDHPS) (6CLV) 和 DNA 旋转酶 (1KZN) 蛋白对合成的化合物进行了分子对接研究。此外，配体与蛋白质研究的结合模式非常有前途。在合成的化合物中，发现化合物5e是最有效的，并且对两种蛋白质 1KZN 和 6CLV 都显示出良好的结合相互作用和最高的对接分数。 图形概要
• Synthesis, characterization and catalytic application of tributyl(carboxymethyl)phosphonium bromotrichloroferrate as a new magnetic ionic liquid for the preparation of 2,3-dihydroquinazolin-4(1H)-ones and 4H-pyrimidobenzothiazoles
  作者：Mohammad Reza Anizadeh、Mohammad Ali Zolfigol、Meysam Yarie、Morteza Torabi、Saeid Azizian

  DOI：10.1007/s11164-020-04183-y

  日期：2020.8

  magnetic ionic liquid bearing acetic acid tags was synthesized and characterized by several methods including Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA) and derivative thermogravimetry analysis (DTG). The prepared magnetic ionic liquid was applied as catalyst for synthesis of 2,3-

  摘要 本文合成了带有乙酸标签的新型三丁基（羧甲基）溴三氯高铁酸fer盐，并通过傅里叶变换红外光谱（FT-IR），能量色散X射线光谱（EDX），振动等方法进行了表征。样品磁力计（VSM），热重分析（TGA）和微分热重分析（DTG）。将所制备的磁性离子液体用作在无溶剂条件下合成2，3-二氢喹唑啉-4（1 H）-ones和4 H-嘧啶基苯并噻唑衍生物的催化剂。 图形摘要 新型磁性离子液体对合成2,3-二氢喹唑啉-4（1 H）-ones和4 H-嘧啶基苯并噻唑衍生物具有很高的催化性能。
• Preparation and characterization of Lewis acid grafted sulfonated carbon@titania composites for the multicomponent synthesis of 4H-pyrimido[2,1-b]benzothiazoles and benzoxanthenones under solvent-free conditions
  作者：Manmeet Kour、Satya Paul、James H. Clark、Vivek K. Gupta、Rajni Kant

  DOI：10.1016/j.molcata.2015.11.001

  日期：2016.1

  A series of novel and highly efficient Lewis acids covalently grafted over sulfonic acid functionalized carbon@titania composites were successfully synthesized via sulfonation of carbon@titania composites followed by treatment with different Lewis acids like AlCl3, FeCl3, SbCl3, SnCl2, Cu(OAc)(2) and Bi(NO3)(3), The utility of the developed catalysts was explored for the synthesis of a diverse range of 4H-pyrimido[2,1-b]benzothiazoles and benzoxanthenones, and among various catalysts, C/TiO2-SO3-SbCl2 was found to be the most active. We report here the synthesis of five novel compounds and the structure of one of the compounds has also been confirmed by single-crystal X-ray diffraction. All the five prepared composites were characterized by FTIR and ICP-AES analysis, whereas the most active one, C/TiO2-SO3-SbCl2 was further characterized by XRD, EDX, CHNS, SEM, TEM, HRTEM and TGA. The catalyst can be recovered and reused for atleast five runs without any significant impact on catalytic activity and selectivity. The high catalytic activity, thermal stability, simple recovery and reusability, and eco-friendly nature of the catalyst makes the present method to be particularly attractive from the view point of green chemistry. (C) 2015 Elsevier B.V. All rights reserved.
• Highly efficient and diversity-oriented solvent-free synthesis of biologically active fused heterocycles using glycerol-based sulfonic acid
  作者：Ayushi Sethiya、Priyanka Kalal、Pankaj Teli、Nusrat Sahiba、Jay Soni、Deepkumar Joshi、Shikha Agarwal

  DOI：10.1007/s11164-022-04822-6

  日期：2022.11

  A series of fused derivatives confirmed the high functional group tolerance of the present protocol. The fabricated pathway has numerous advantages like high yields of desired products, green, solvent-free, and use of easily recoverable and reusable heterogeneous catalyst. Further, the anti-microbial results confirmed that among the synthesized compounds, compounds 4c and 6a were found more active

  本文涉及在催化量的甘油基磺酸中使用芳香醛、1,3-环二酮（二甲酮/环己二酮）和脲/2-氨基苯并噻唑制备一些新型稠合喹唑啉类似物。通过使用甘油基磺酸作为催化剂，金属污染的威胁已被根除。这种 MCR 策略的假定机制类似于 Biginelli 反应，包括 Knoevenagel 缩合和 Michael 加成。一系列融合衍生物证实了本协议的高官能团耐受性。制备的途径具有许多优点，如所需产物的高收率、绿色、无溶剂以及使用易于回收和可重复使用的多相催化剂。更远，发现与环丙沙星相比，4c和6a对测试的细菌菌株更有活性。与氟康唑相比，发现化合物4g和6a对测试的真菌菌株更有活性。 图形概要