3-(2-phenylthiazol-5-yl)-pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-phenylthiazol-5-yl)-pyridine
• 英文别名: 3-(2-phenylthiazol-5-yl)pyridine；2-Phenyl-5-pyridin-3-yl-1,3-thiazole；2-phenyl-5-pyridin-3-yl-1,3-thiazole
• 化学式: C₁₄H₁₀N₂S
• 分子量: 238.313
• InChiKey: LKTUDKGCBICCMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-碘吡啶 、 2-苯基噻唑 在 [Pd((diphenylphosphanyl)ferrocene)Cl₂]*CH₂Cl₂ 三苯基膦 、 silver carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 以99%的产率得到3-(2-phenylthiazol-5-yl)-pyridine
  参考文献：
  名称：

  噻唑在水中直接芳基化。

  摘要：

  DOI：

  10.1002/anie.200702141

文献信息

• Comparing the Reactivity of the 4- and 5-Positions of 2-Phenylthiazoles in Stille Cross-Coupling Reactions
  作者：Peter Stanetty、Johanna Hämmerle、Michael Schnürch

  DOI：10.1055/s-2007-990972

  日期：2007.12

  A systematic study of the cross-coupling capability of 4- and 5-substituted 2-phenylthiazoles under Stille conditions is presented. Two cross-coupling options were investigated: 1) combination of thiazolylstannanes with various aryl(hetaryl) halides and, 2) reaction of halothiazoles with PhSn(Bu)3 as coupling partner. The results obtained from the cross-coupling reactions on the 4- and 5-positions of the thiazole system were compared regarding the influence of the position of the halide (Br, I) and the Bu3Sn group on both coupling partners. A broad selection of aromatic and heteroaromatic halides was coupled in order to establish a general reactivity platform for this heterocyclic system.

  本文系统研究了在Stille反应条件下4-和5-取代的2-苯基噻唑的交叉偶联能力。研究了两种交叉偶联选项：1）噻唑基锡化物与各种芳基（杂芳基）卤化物的组合；2）以PhSn(Bu)3作为偶联伙伴进行卤噻唑的反应。比较了在噻唑体系的4位和5位上的交叉偶联反应的结果，分析了卤化物（溴、碘）和Bu3Sn基团在两种偶联伙伴上的位置影响。通过偶联大量芳香和杂芳香卤化物，建立了该杂环体系的一般反应性平台。
• A Comparative Study on Stille Cross-Coupling Reactions of 2-Phenylthiazoles and 2-Phenyloxazoles
  作者：Peter Stanetty、Johanna Hämmerle、Markus Spina、Michael Schnürch、Marko Mihovilovic

  DOI：10.1055/s-2008-1067263

  日期：2008.10

  A systematic study of the cross-coupling capability of the 4- and 5-positions of 2-phenylthiazoles and -oxazoles under Stille conditions is presented. The azoles were both applied as stannanes and as the halide component. The obtained results were compared regarding the position of the halide and Bu3Sn group. In order to establish a general reactivity platform for those heterocyclic systems, a broad variety of aromatic and heteroaromatic halides were coupled and some significant differences concerning the coupling properties of the investigated systems were observed.

  本文系统研究了在Stille条件下2-苯基噻唑和-噁唑的4位和5位的交叉偶联能力。噁唑既可用作锡烷，也可用作卤化物成分。将所得结果与卤化物和Bu3Sn基团的位置进行了比较。为了建立这些杂环系统的通用反应平台，对多种芳香和杂芳卤化物进行了偶联，并观察到所研究系统的偶联性质存在一些显著差异。
• A Systematic Study of Suzuki-Miyaura Cross-Coupling Reactions on Thiazoleboronic Esters in the 4- and 5-Position
  作者：Michael Schnürch、Johanna Hämmerle、Marko Mihovilovic、Peter Stanetty

  DOI：10.1055/s-0029-1218598

  日期：2010.3

  reaction of thiazoleboronic esters under microwave conditions is presented. Boronic acid esters were prepared in the 4- and 5-position of the thiazole ring and subsequently cross-coupled with a number of different (hetero)aryl halides. Yields of the coupling process depended on the reactivity of the boronic acid at the particular position in the thiazole system, as hydrolysis and subsequent deboronation

  提出了在微波条件下噻唑硼酸酯的Suzuki-Miyaura交叉偶联反应的系统研究。在噻唑环的4-位和5-位制备硼酸酯，然后与许多不同的（杂）芳基卤化物进行交叉偶联。偶联过程的产率取决于噻唑体系中特定位置的硼酸的反应性，因为发现水解和随后的脱硼是主要的副反应。 交叉偶联-均相催化-杂环-钯-锂化
• A guideline for the arylation of positions 4 and 5 of thiazole via Pd-catalyzed cross-coupling reactions
  作者：Johanna Hämmerle、Michael Schnürch、Naseer Iqbal、Marko D. Mihovilovic、Peter Stanetty

  DOI：10.1016/j.tet.2010.07.081

  日期：2010.10

  The arylation of thiazoles in 4- and 5-position was investigated in detail. Suzuki-Miyaura and Stille cross-coupling reactions were tested using thiazoles either as halide or organometal species. The obtained results were critically compared to develop helpful guidelines for selection of the cross-coupling methodology with the best potential for good and reliable results for a given synthetic problem without the need for tedious optimization of reaction parameters. (C) 2010 Elsevier Ltd. All rights reserved.