2-phenyl-4-(thiophen-2-yl)thiazol-5-amine | 1041436-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4-(thiophen-2-yl)thiazol-5-amine
• 英文别名: 2-phenyl-4-thiophen-2-ylthiazol-5-ylamine；2-Phenyl-4-thiophen-2-yl-1,3-thiazol-5-amine
• CAS: 1041436-10-5
• 化学式: C₁₃H₁₀N₂S₂
• 分子量: 258.368
• InChiKey: UPXRYINZZDGADJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  95.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(thiophen-2-yl)thiazol-5-amine 、 2-三氟甲基苯甲酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以87 mg的产率得到N-(2-phenyl-4-(thiophen-2-yl)thiazol-5-yl)-2-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Ugi Reactions with Ammonia Offer Rapid Access to a Wide Range of 5-Aminothiazole and Oxazole Derivatives

  摘要：

  A series of Ugi reactions has been successfully performed using ammonia as the amine component, employing 2,2,2-trifluoroethanol its a non-nucleophilic solvent in order to suppress known side reactions. Utilizing concentrated aqueous ammonia its it convenient Source, this approach offered a simple, one-step assembly of Ugi adducts suitable for elaboration into it variety of 5-aminoazole compounds through postcondensation modifications. Free or N-substituted 5-aminothiazoles and 5-(trifluoroacetamido)oxazoles were all prepared by this improved methodology. The scope of the synthetic route developed and application of the different products are discussed.

  DOI：

  10.1021/jo9014529
• 作为产物：
  描述：

  (2-phenyl-4-thiophen-2-ylthiazol-5-yl)-(1,1,3,3-tetramethylbutyl)amine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以50%的产率得到2-phenyl-4-(thiophen-2-yl)thiazol-5-amine
  参考文献：
  名称：

  Versatile assembly of 5-aminothiazoles based on the Ugi four-component coupling

  摘要：

  A flexible route to novel 5-aminothiazoles has been developed based on cyclisation of diamide adducts, prepared using the Ugi reaction, in the presence of Lawesson's reagent. The Walborsky reagent ( 1,1,3,3-tetramethylbutyl isocyanide) was used as the isonitrile component, facilitating subsequent deprotection of the N-alkyl group to yield free 5-aminothiazoles, which were prepared with a variety of substituents at the 2- and 4-positions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.067

文献信息

• [EN] THIAZOLE AND OXAZOLE DERIVATIVES FOR USE IN THE TREATMENT OF PRION DISEASES, CANCER AND CONDITIONS OF THE CENTRAL NERVOUS SYSTEM AS WELL AS IN THE REGULATION OF STEM CELLS<br/>[FR] DÉRIVÉS DE THIAZOLE ET D'OXAZOLE S'UTILISANT DANS LE TRAITEMENT DE MALADIES À PRIONS, DU CANCER ET DE TROUBLES DU SYSTÈME NERVEUX CENTRAL, ET DANS LA RÉGULATION DE CELLULES SOUCHES
  申请人：UNIV SHEFFIELD

  公开号：WO2008090382A1

  公开（公告）日：2008-07-31

  [EN] Compounds of the formula (I) are provided: Fomula (I) wherein X, Y, R1, R2 and R3 are as defined in the specification. The compounds may be useful in the treatment of various diseases and conditions, in particular prion diseases.
  [FR] L'invention concerne des composés représentés par la formule (I), dans laquelle X, Y, R1, R2 et R3 sont tels que définis dans la description. Ces composés peuvent être utiles dans le traitement de diverses maladies et affections, en particulier les maladies à prions.
• Ugi Reactions with Ammonia Offer Rapid Access to a Wide Range of 5-Aminothiazole and Oxazole Derivatives
  作者：Mark J. Thompson、Beining Chen

  DOI：10.1021/jo9014529

  日期：2009.9.18

  A series of Ugi reactions has been successfully performed using ammonia as the amine component, employing 2,2,2-trifluoroethanol its a non-nucleophilic solvent in order to suppress known side reactions. Utilizing concentrated aqueous ammonia its it convenient Source, this approach offered a simple, one-step assembly of Ugi adducts suitable for elaboration into it variety of 5-aminoazole compounds through postcondensation modifications. Free or N-substituted 5-aminothiazoles and 5-(trifluoroacetamido)oxazoles were all prepared by this improved methodology. The scope of the synthetic route developed and application of the different products are discussed.
• Versatile assembly of 5-aminothiazoles based on the Ugi four-component coupling
  作者：Mark J. Thompson、Beining Chen

  DOI：10.1016/j.tetlet.2008.06.067

  日期：2008.9

  A flexible route to novel 5-aminothiazoles has been developed based on cyclisation of diamide adducts, prepared using the Ugi reaction, in the presence of Lawesson's reagent. The Walborsky reagent ( 1,1,3,3-tetramethylbutyl isocyanide) was used as the isonitrile component, facilitating subsequent deprotection of the N-alkyl group to yield free 5-aminothiazoles, which were prepared with a variety of substituents at the 2- and 4-positions. (C) 2008 Elsevier Ltd. All rights reserved.