6-(4-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole | 92754-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole
• 英文别名: 6-(4-Methoxyphenyl)-3-methylimidazo[2,1-b][1,3]thiazole
• CAS: 92754-14-8
• 化学式: C₁₃H₁₂N₂OS
• mdl: MFCD01924852
• 分子量: 244.317
• InChiKey: OMBZQHQRYNULQF-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C(Solv: ethanol (64-17-5))
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole 在 盐酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 8-Hydroxy-8-(4-methoxy-phenyl)-5-methyl-8H-[1,2,4]oxadiazolo[3,4-c][1,4]thiazin-3-one
  参考文献：
  名称：

  Ring-ring interconversions. Part 2. Effect of the substituent on the rearrangement of 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles into 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c][1,2,4]oxadiazol-3-ones. A novel class of potential antitumor agents

  摘要：

  The reaction of several 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles with hydrochloric acid by refluxing in ethanol gives new 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c] [1,2,4]oxadiazol-3-ones for testing of their biological activity. By carrying out the reaction at room temperature it has been possible to isolate reaction intermediates to which structures have been assigned. This study has provided information on the reaction mechanism and on the effect of the substituent in the phenyl ring on the yield of the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00189-1
• 作为产物：
  描述：

  2-(2-Imino-4-methyl-thiazol-3-yl)-1-(4-methoxy-phenyl)-ethanone; hydrobromide 在 氢溴酸 作用下， 反应 1.0h， 生成 6-(4-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Andreani; Rambaldi; Bonazzi, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 219 - 222

  摘要：

  DOI：

文献信息

• Palladium-catalyzed site-selective C H alkenylation of imidazo[2,1-b]thiazoles
  作者：Guoli Huang、Mingyu Teng、Bo Liu、Meizhu Rong、Ying Liu、Yegao Chen

  DOI：10.1016/j.jorganchem.2016.06.014

  日期：2016.9

  Dehydrogenative alkenylation of imidazo[2,1-b]thiazoles via palladium(II)-catalyzed site-selective CH bond activation has been developed in moderate to good yields under aerobic conditions. This methodology provides a very efficient, direct, and atomeconomical strategies to construct an alkenyl-imidazo[2,1-b]thiazole moiety.

  咪唑并[2,1- b ]噻唑经钯（II）催化的位点选择性C H键活化脱氢烯基化反应在需氧条件下以中等至良好的收率得到了发展。该方法学提供了一种非常有效，直接和经济的方法来构建烯基-咪唑并[2,1- b ]噻唑部分。
• Microwave-assisted and catalyst-free sulfenylation of imidazo[2,1-<i>b</i>]thiazoles with sulfonyl hydrazides in water
  作者：Shaohua Wang、Run Luo、Lina Guo、Tianxi Zhu、Xu Chen、Wenjie Liu

  DOI：10.1080/10426507.2020.1768537

  日期：2020.10.2

  Abstract An efficient microwave-assisted and catalyst-free sulfenylation of imidazo[2,1-b]thiazoles with sulfonyl hydrazides has been developed in water. This method is practical and environmental friendly, and can be performed within a short reaction time. The sulfenylation reaction shows high regioselectivity, and excellent functional-group compatibility, giving the desired products in moderate to

  摘要 在水中开发了一种有效的微波辅助和无催化剂的咪唑并 [2,1-b] 噻唑与磺酰肼的磺酰化反应。该方法实用、环保，反应时间短。磺酰化反应显示出高区域选择性和优异的官能团兼容性，以中等至良好的产率得到所需的产物。图形摘要
• Regioselective palladium-catalyzed phosphonation of imidazo[2,1-b]thiazoles with dialkyl phosphites
  作者：Wenjie Liu、Shaohua Wang、Huagang Yao、Ziying Li、Yanling Huang、Chunyun Kong

  DOI：10.1016/j.tetlet.2015.09.078

  日期：2015.10

  A novel and facile Pd-catalyzed direct phosphonation of imidazo[2,1-b]thiazoles with dialkyl phosphites has been developed to give the corresponding C-5 phosphonated products in moderate to good yields with high regioselectivity.

  已开发了一种新颖且简便的Pd催化的咪唑并[2,1-b]噻唑与亚磷酸二烷基酯的直接膦化反应，以中等至良好的收率和较高的区域选择性提供了相应的C-5膦酸酯化产物。
• Oxone®-mediated direct arylselenylation of imidazo[2,1-b]thiazoles, imidazo[1,2-a]pyridines and 1H-pyrazoles
  作者：Ingrid Rodrigues、Angelita M. Barcellos、Andrei L. Belladona、Juliano A. Roehrs、Roberta Cargnelutti、Diego Alves、Gelson Perin、Ricardo F. Schumacher

  DOI：10.1016/j.tet.2018.06.046

  日期：2018.8

  Oxone mediated reaction of imidazo[2,1-b]thiazole, imidazo[1,2-a]pyridine and 1H-pyrazole derivatives with diaryl diselenides is presented here. The methodology represents an efficient and simple protocol for carrying out the selective synthesis of 5-arylselanyl-imidazo[2,1-b]thiazoles, 3-arylselanyl-imidazo[1,2-a]pyridines and 4-arylselanyl-1H-pyrazoles in high yields using a stable, nontoxic and

  本文介绍了由氧酮介导的咪唑并[2,1- b ]噻唑，咪唑并[1,2- a ]吡啶和1 H-吡唑衍生物与二芳基二硒化物的反应。该方法表示用于执行5- arylselanyl -咪唑并[2,1-的选择性合成的有效和简单的协议b ]噻唑，3- arylselanyl -咪唑并[1,2一]吡啶和4- arylselanyl-1 ħ -使用稳定，无毒且廉价的氧化剂，可高产率生产吡唑。该反应在60℃下在空气中使用乙腈作为溶剂进行。替代地，超声辐射的使用被提出为用于快速且有效的能量转移的工具，其显着减少了反应时间。
• Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine
  作者：Haibo Mei、Chen Xie、Lingmin Wu、Vadim A. Soloshonok、Jianlin Han、Yi Pan

  DOI：10.1039/c3ob41785a

  日期：——

  reasonably good yields (55%–79%) and exceptionally high stereoselectivity (>99 : 1 dr). This method presents a general approach for the preparation of a new type of biologically relevant compounds containing pharmacophoric imidazo[2,1-b]thiazole and (trifluoro)ethylamine groups.

  咪唑并[2,1-的不对称曼尼希反应b ]噻唑衍生的亲核试剂与（S小号） - N-叔-butanesulfinyl（3,3,3-）-trifluoroacetaldimine发现具有相当好的产率继续进行（55％-79％ ）和极高的立体选择性（> 99：1 dr）。该方法为制备含有药效基咪唑并[2，1- b ]噻唑和（三氟）乙胺基团的新型生物相关化合物提供了一种通用方法。