N-allyl-benzo[d]oxazol-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-allyl-benzo[d]oxazol-2-amine
• 英文别名: N-allylbenzo[d]oxazol-2-amine；N-2-propen-1-yl-2-benzoxazolamine；N-prop-2-enyl-1,3-benzoxazol-2-amine
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD16661784
• 分子量: 174.202
• InChiKey: TUQBWFRTADXZBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-allyl-benzo[d]oxazol-2-amine 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 以50%的产率得到N-丙基-1,3-苯并恶唑-2-胺
  参考文献：
  名称：

  Facile Rearrangements of Alkynylamino Heterocycles with Noble Metal Cations

  摘要：

  A number of 2-(alkynylamino)-substituted heterocycles have been synthesized. These heterocycles rearrange in the presence of silver(I) and gold(I) salts to give novel 2H-pyrimido[2,1-b]benzoxazoles, 2H-pyrimido[2,1-b]benzothiazoles, and a 2H-pyrimido[2,1-b]benzoselenazole. Two of the the 2H-pyrimido[2,1-b]benzoxazoles were isolated in good yield. The kinetics of the silver tetrafluoroborate-catalyzed rearrangements of selected (alkynylamino)benzoxazoles and benzothiazoles have been examined by H-1 NMR in CD3CN. Factors affecting the electron densities of the triple bond and of the nitrogen atom in the heterocycle are important in influencing the rate of rearrangement.

  DOI：

  10.1021/jo952101z
• 作为产物：
  描述：

  2-氯苯并恶唑 、 丙烯胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以48%的产率得到N-allyl-benzo[d]oxazol-2-amine
  参考文献：
  名称：

  Facile Rearrangements of Alkynylamino Heterocycles with Noble Metal Cations

  摘要：

  A number of 2-(alkynylamino)-substituted heterocycles have been synthesized. These heterocycles rearrange in the presence of silver(I) and gold(I) salts to give novel 2H-pyrimido[2,1-b]benzoxazoles, 2H-pyrimido[2,1-b]benzothiazoles, and a 2H-pyrimido[2,1-b]benzoselenazole. Two of the the 2H-pyrimido[2,1-b]benzoxazoles were isolated in good yield. The kinetics of the silver tetrafluoroborate-catalyzed rearrangements of selected (alkynylamino)benzoxazoles and benzothiazoles have been examined by H-1 NMR in CD3CN. Factors affecting the electron densities of the triple bond and of the nitrogen atom in the heterocycle are important in influencing the rate of rearrangement.

  DOI：

  10.1021/jo952101z

文献信息

• A Metal-Free Oxidative Amination of Benzoxazoles with Primary Amines and Ammonia
  作者：Boris Nachtsheim、Ulrich Kloeckner、Nicole Weckenmann

  DOI：10.1055/s-0031-1289902

  日期：2012.1

  An efficient synthesis of 2-aminobenzoxazoles is described by a direct oxidative amination of unfunctionalized benzoxazoles with primary amines. The reaction could be performed in the absence of transition metals by using catalytic amounts of a quaternary ammonium iodide and tert-butylhydroperoxide as a cheap and easy-to-handle co-oxidant. In addition to primary amines, aqueous solutions of NH3 were used to introduce a primary amine group into the heterocyclic core.

  报道了一种高效的2-氨基苯并噁唑合成方法，通过未官能化的苯并噁唑与伯胺直接氧化胺化实现。该反应在无需过渡金属存在的情况下，使用催化量的季铵碘盐和叔丁基过氧化氢作为廉价且易于处理的共氧化剂即可进行。除了伯胺，水溶液中的氨也被用来向杂环核心引入伯胺基团。
• Synthesis of 2-Aminobenzoxazoles Using Tetramethyl Orthocarbonate or 1,1-Dichlorodiphenoxymethane
  作者：Christopher L. Cioffi、John J. Lansing、Hamza Yüksel

  DOI：10.1021/jo1017052

  日期：2010.11.19

  The synthesis of 2-aminobenzoxazoles can be readily achieved by two versatile, one-pot procedures utilizing commercially available tetramethyl orthocarbonate or 1,1-dichlorodiphenoxymethane, an amine, and an optionally substituted 2-aminophenol. The reactions were conducted under mild conditions and provided 2-aminobenzoxazoles in modest to excellent yields. A variety of amines and substituted 2-aminophenols

  2-氨基苯并恶唑的合成可以容易地通过两种通用的一锅法，利用市售的原碳酸四甲酯或1，1-二氯二苯氧基甲烷，胺和任选取代的2-氨基苯酚来完成。反应在温和的条件下进行，以适中至优异的产率提供了2-氨基苯并恶唑。各种胺和取代的2-氨基苯酚用于研究反应范围。
• [EN] SYNTHESIS OF 2-AMINOBENZOXAZOLE COMPOUNDS<br/>[FR] SYNTHÈSE DE COMPOSÉS DE 2-AMINO-BENZOXAZOLE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2010048514A1

  公开（公告）日：2010-04-29

  A method for forming an optionally substituted 2-aminobenzoxazole compound includes: contacting an optionally substituted 2-aminophenol compound with (1) an amine of the formula NHR2R3, wherein R2 and R3 are each independently selected from H, an optionally substituted alkyl group or an optionally substituted aryl group, or R2 and R3, taken together with the nitrogen atom to which they are attached, form an optionally substituted heterocyclic ring; and (2) a reactant selected from the group consisting of: (a) C(OR)4, wherein R represents an alkyl group; (b) C(OAr)4, wherein Ar represents an aryl group; and (c) CCl2(OAr)2, wherein Ar represents an aryl group, in combination with a base; thereby forming the optionally substituted 2-aminobenzoxazole compound.

  一种形成可选择取代的2-氨基苯并噁唑化合物的方法包括：将可选择取代的2-氨基苯酚化合物与（1）符合NHR2R3公式的胺接触，其中R2和R3分别独立地选自H、可选择取代的烷基或可选择取代的芳基，或者R2和R3与它们连接的氮原子一起形成可选择取代的杂环环；以及（2）选自以下组合的反应物：（a）C（OR）4，其中R代表烷基；（b）C（OAr）4，其中Ar代表芳基；和（c）CCl2（OAr）2，其中Ar代表芳基，结合碱；从而形成可选择取代的2-氨基苯并噁唑化合物。
• Control of selectivity in the preparation of 2-substituted benzoazoles by adjusting the surface hydrophobicity in two solid-based sulfonic acid catalysts
  作者：Babak Karimi、Akbar Mobaraki、Hamid M. Mirzaei、Hojatollah Vali

  DOI：10.1039/d2ob02274e

  日期：——

  A series of metal-free tandem reactions for the synthesis of pharmaceutically important 2-substituted benzoazoles from isothiocyanates and 2-aminothiophenol under catalyst-free conditions in the presence of Et-PMO-Me-PrSO3H (1a) and SBA-15-PrSO3H (1b) as solid acids were carried out in a highly selective way under solvent free conditions. A significant selectivity changeover toward either 2-mercaptobenzoxazole

  在 Et-PMO-Me-PrSO 3 H ( 1a ) 和 SBA-15-存在下，在无催化剂条件下，从异硫氰酸酯和 2-氨基苯硫酚合成药学上重要的 2-取代苯并唑的一系列无金属串联反应PrSO 3 H ( 1b ) 作为固体酸在无溶剂条件下以高度选择性的方式进行。通过将使用的催化剂从相对疏水的材料1a改为更亲水的催化剂1b，可以实现对 2-巯基苯并恶唑或 2-氨基苯并唑衍生物的显着选择性转换. 这种简单的实验程序采用新颖的苯并唑选择性方法，并辅以绿色和可重复使用的催化剂，可被视为现有 2-取代苯并唑衍生物合成方法的替代方法。
• NEUE BENZIMIDAZOL-2-YL-ALKYLAMINE UND IHRE ANWENDUNG ALS MIKROBIZIDE WIRKSTOFFE
  申请人：EMC microcollections GmbH

  公开号：EP2193123A1

  公开（公告）日：2010-06-09