2-(furan-3-yl)benzo[d]thiazole

• 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-(furan-3-yl)benzo[d]thiazole
• 英文别名: 2-(furan-3-yl)benzothiazole；2-(furan-3-yl)-1,3-benzothiazole
• 化学式: C₁₁H₇NOS
• 分子量: 201.249
• InChiKey: GTWBSRSFWXKFPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-糠醛 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 反应 2.0h， 以90%的产率得到2-(furan-3-yl)benzo[d]thiazole
  参考文献：
  名称：

  A Simple and Efficient Synthesis of (Hetero)Aryl-Substituted Benzothiazolyl or Benzoxazolyl Furan, Thiophene and N-methylpyrrole Derivatives through a Palladium-Catalyzed Regioselective C–H Bond Arylation

  摘要：

  The synthesis of 2-(hetero)aryl-5-benzothiazol-2-yl or -benzoxazol-2-ylfuran, -thiophene, and -1-methylpyrrole derivatives was accomplished in two steps. 2-(Benzothiazol-2-yl)- or 2-benzoxazol-2-ylfuran, -thiophene, or -1-methylpyrrole were synthesized by coupling a heteroaryl aldehyde and either 2-mercaptophenol or 2-aminophenol. Then, they were successfully arylated with a wide range of aryl bromides using a phosphine-free palladium protocol; regioselective arylation at C5 of furan, thiophene, or 1-methyl-1H-pyrrole was observed in all cases. This reaction tolerates a wide variety of substituents on the aryl bromides as well as heteroaryl bromides.

  DOI：

  10.1055/s-0034-1379021

文献信息

• Pd-Catalyzed Decarbonylative C−H Coupling of Azoles and Aromatic Esters
  作者：Kaoru Matsushita、Ryosuke Takise、Tomoya Hisada、Shin Suzuki、Ryota Isshiki、Kenichiro Itami、Kei Muto、Junichiro Yamaguchi

  DOI：10.1002/asia.201800478

  日期：2018.9.4

  decarbonylative C−H coupling of azoles and aromatic esters by palladium catalysis is described. Our previously reported Ni‐catalyzed C−H coupling of azoles and aromatic esters has a significant drawback regarding the substrate scope. Herein, we employ palladium catalysis instead of nickel, resulting in a broader substrate scope in terms of azoles and aromatic esters.

  描述了通过钯催化的唑和芳族酯的脱羰CH键偶联。我们先前报道的唑和芳族酯的Ni催化的CH偶联在底物范围方面存在重大缺陷。在本文中，我们使用钯催化代替镍，从而在吡咯和芳族酯方面产生了更广阔的底物范围。
• One-Pot Synthesis of 2-Aryl- and 2-Alkylbenzothiazoles under Microwave Irradiation
  作者：Edward R. Biehl、Sukanta Kamila、Hongming Zhang

  DOI：10.3987/com-05-10466

  日期：——

  Eco-friendly direct solvent-free reactions of o-aminothiophenol and aromatic or aliphatic β-keto esters with microwave irradiation produced 2-substituted benzothiazoles in excellent yield. Experiments that compared microwave irradiation to conventional heating methods showed that the former gives the 2-substituted benzothiazoles faster and in higher yields. The formation of the titled compounds probably

  邻氨基苯硫酚和芳香族或脂肪族 β-酮酯在微波辐射下的环保直接无溶剂反应以优异的产率产生 2-取代的苯并噻唑。将微波辐射与传统加热方法进行比较的实验表明，前者更快地产生 2-取代的苯并噻唑，产率更高。标题化合物的形成可能涉及将硫醇基团亲核加成到 β-酮酯的酮基上，随后从所得加合物中消除乙酸乙酯。然后加合物经历邻氨基与羰基的分子内加成，得到加合物，从加合物中除去水，得到2-取代的苯并噻唑。
• Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions
  作者：Masayuki Kubo、Naomi Inayama、Eisuke Ota、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.2c01432

  日期：2022.6.3

  “Dance reaction” on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and

  芳环上的“舞蹈反应”是有机化学中转移芳烃支架上官能团的有效方法。值得注意的是，卤化物和拟卤化物的舞蹈反应在与过渡金属催化的偶联反应结合时，为取代（杂）芳族化合物的不同合成提供了独特的平台。在此，我们报告了由钯催化实现的酯舞和脱羰基偶联的串联反应。在该反应中，芳环上的酯部分发生 1,2-易位后，与亲核试剂发生脱羰偶联，从而能够在起始材料中与酯相邻的位置安装各种亲核试剂。