2-(1-Benzofuran-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole | 1170007-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-(1-Benzofuran-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
• CAS: 1170007-22-3
• 化学式: C₁₆H₉ClN₂O₂
• 分子量: 296.713
• InChiKey: VYXXMPUCEKIJQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-氯苯基)-1,3,4-噁二唑 、 2-(2,2-dibromovinyl)phenol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(I) bromide 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以92%的产率得到2-(1-Benzofuran-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Highly efficient copper/palladium-catalyzed tandem Ullman reaction/arylation of azoles via C–H activation: synthesis of benzofuranyl and indolyl azoles from 2-(gem-dibromovinyl)phenols(anilines) with azoles

  摘要：

  In this paper, a novel and highly efficient copper/palladium-catalyzed tandem intramolecular Ullman-type C-O(N) coupling reaction of 2-(gem-dibromovinyl)phenols(anilines) followed by an intermolecular arylation of azoles through C-H activation has been developed. In the presence of CuBr with Pd(PPh3)(2)Cl-2 used as co-catalyst, and (LiOBu)-Bu-t as a base, the one-pot reactions of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)anilines with a variety of azoles, including oxazoles, imidazoles, thiazoles, and oxadiazoles underwent smoothly in toluene at 100 degrees C to generate the corresponding biheteroaryl products in high yields. A tentative mechanism of copper/palladium-catalyzed tandem reaction was described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.044

文献信息

• Utilization of 2-benzo[<i>b</i>]furan carboxylic acid hydrazide in the synthesis of 1,3,4-oxadiazole derivatives
  作者：Yu-Xia Da、Zhi Yang、Zheng-Jun Quan、Zhang Zhang、Xi-Cun Wang

  DOI：10.1002/jhet.142

  日期：2009.7

  In this study, the synthesis of series of 2-benzo[b]furan-substituted 1,3,4-oxadiazole derivatives using readily available 2-benzo[b]furan carboxylic acid hydrazide as starting material has been investigated. J. Heterocyclic Chem., (2009).

  在这项研究中，已经研究了以容易获得的2-苯并[ b ]呋喃羧酸酰肼为起始原料合成一系列2-苯并[ b ]呋喃取代的1,3,4-恶二唑衍生物的方法。J.杂环化​​学，（2009）。
• Highly efficient copper/palladium-catalyzed tandem Ullman reaction/arylation of azoles via C–H activation: synthesis of benzofuranyl and indolyl azoles from 2-(gem-dibromovinyl)phenols(anilines) with azoles
  作者：Wei Chen、Min Wang、Pinhua Li、Lei Wang

  DOI：10.1016/j.tet.2011.06.044

  日期：2011.8

  In this paper, a novel and highly efficient copper/palladium-catalyzed tandem intramolecular Ullman-type C-O(N) coupling reaction of 2-(gem-dibromovinyl)phenols(anilines) followed by an intermolecular arylation of azoles through C-H activation has been developed. In the presence of CuBr with Pd(PPh3)(2)Cl-2 used as co-catalyst, and (LiOBu)-Bu-t as a base, the one-pot reactions of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)anilines with a variety of azoles, including oxazoles, imidazoles, thiazoles, and oxadiazoles underwent smoothly in toluene at 100 degrees C to generate the corresponding biheteroaryl products in high yields. A tentative mechanism of copper/palladium-catalyzed tandem reaction was described. (C) 2011 Elsevier Ltd. All rights reserved.