5-(furan-2-yl)-1-phenyl-1H-tetrazole | 332176-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(furan-2-yl)-1-phenyl-1H-tetrazole
• 英文别名: 5-(Furan-2-yl)-1-phenyltetrazole
• CAS: 332176-11-1
• 化学式: C₁₁H₈N₄O
• 分子量: 212.211
• InChiKey: HHFOBGAKIWPJJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 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：
  56.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  呋喃-2-硫代甲酸苯胺 在 三乙胺 、 2-碘酰基苯甲酸 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到5-(furan-2-yl)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  o-Iodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles

  摘要：

  A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.

  DOI：

  10.1021/jo2025509

文献信息

• Transition-metal-free multinitrogenation of amides by C–C bond cleavage: a new approach to tetrazoles
  作者：Lian-Hua Li、Zhi-Jie Niu、Ying-Xiu Li、Yong-Min Liang

  DOI：10.1039/c8cc06324a

  日期：——

  regioselective synthesis of 1,5-disubstituted tetrazoles has been developed. By means of electrophilic amide activation, and further C–C bond cleavage and rearrangement, a diverse set of functionalized 1,5-DST derivatives were selectively constructed under mild conditions. As showcased in the mechanisms, the chemoselectivity is easily switched by the selection of the starting materials in the reaction.

  开发了一种无金属的全新的一锅多酰胺酰胺，用于化学和区域选择性合成1,5-二取代的四唑。通过亲电酰胺的活化，以及进一步的C–C键裂解和重排，在温和条件下选择性地构建了多种功能化的1,5-DST衍生物。如机理所示，通过选择反应中的起始原料可以容易地切换化学选择性。
• Synthesis of 1,5-disubstituted tetrazoles via Suzuki–Miyaura cross-coupling of 5-chloro-1-phenyltetrazole
  作者：Qing Tang、Ryan Gianatassio

  DOI：10.1016/j.tetlet.2010.04.091

  日期：2010.7

  Suzuki–Miyaura coupling reactions of 5-chloro-1-phenyl-tetrazole with various functionalized arylboronic acids were investigated. In the presence of catalytic amounts of SPhos/Pd(OAc)2 or RuPhos/Pd(OAc)2, the reaction proceeded smoothly to afford 1,5-diaryltetrazoles in good to excellent yields.

  研究了5-氯-1-苯基-四唑与各种官能化的芳基硼酸的Suzuki-Miyaura偶联反应。在催化量的SPhos / Pd（OAc）2或RuPhos / Pd（OAc）2的存在下，反应平稳进行，以良好的产率至优异的产率得到1，5-二芳基四唑。
• <i>o</i>-Iodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles
  作者：Pramod S. Chaudhari、Sagar P. Pathare、Krishnacharaya G. Akamanchi

  DOI：10.1021/jo2025509

  日期：2012.4.20

  A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.