1-(2-azidophenyl)-2-(n-butylamino)-2-oxoethyl benzoate | 1193490-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-azidophenyl)-2-(n-butylamino)-2-oxoethyl benzoate
• CAS: 1193490-52-6
• 化学式: C₁₉H₂₀N₄O₃
• 分子量: 352.393
• InChiKey: GCHFBLMNBYFTQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  104.16
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-azidophenyl)-2-(n-butylamino)-2-oxoethyl benzoate 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 26.0h， 以89%的产率得到N-(n-butyl)-2-phenyl-4H-3,1-benzoxazine-4-carboxamide
  参考文献：
  名称：

  New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence

  摘要：

  alpha-Acyloxy-carboxamide azides 1, obtained from Passerini reaction of easily accessible o-azidobenzaldehyde with isocyanides and carboxylic acids, reacted with triphenylphosphine to give various 4-aminocarbonyl substituted 4H-1,3-benzoxazines 3 in moderate to high yields via sequential Staudinger and intramolecular aza-Wittig reaction. However, alpha-hydroxy carboxamide azides 5 were obtained in moderate yields when pyruvic acid was used in the Passerini reaction. Further sequential reaction of azides 5 with triphenylphosphine and isocyanates produced 2-amino-4-aminocarbonyl substituted 4H-1,3-benzoxazines 8 via a tandem Staudinger/aza-Wittig/heterocumulene-mediated annulation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.022
• 作为产物：
  描述：

  异腈基正丁烷 、 2-叠氮基苯甲醛 、 苯甲酸 以 甲醇 为溶剂， 反应 24.0h， 以78%的产率得到1-(2-azidophenyl)-2-(n-butylamino)-2-oxoethyl benzoate
  参考文献：
  名称：

  New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence

  摘要：

  alpha-Acyloxy-carboxamide azides 1, obtained from Passerini reaction of easily accessible o-azidobenzaldehyde with isocyanides and carboxylic acids, reacted with triphenylphosphine to give various 4-aminocarbonyl substituted 4H-1,3-benzoxazines 3 in moderate to high yields via sequential Staudinger and intramolecular aza-Wittig reaction. However, alpha-hydroxy carboxamide azides 5 were obtained in moderate yields when pyruvic acid was used in the Passerini reaction. Further sequential reaction of azides 5 with triphenylphosphine and isocyanates produced 2-amino-4-aminocarbonyl substituted 4H-1,3-benzoxazines 8 via a tandem Staudinger/aza-Wittig/heterocumulene-mediated annulation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.022

文献信息

• New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4<i>H</i>-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence
  作者：Long Zhao、Mao-Lin Yang、Min Liu、Ming-Wu Ding

  DOI：10.3762/bjoc.18.32

  日期：——

  A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes 1, benzoic acid (2), and isocyanides 3 produced the azide intermediates 4, which were treated sequentially with triphenylphosphine

  开发了一种通过顺序 Passerini/Staudinger/aza-Wittig/加成/亲核取代反应高效合成多取代 3,4-二氢喹唑啉和 4 H -3,1-苯并噻嗪的新方法。2-叠氮基苯甲醛1、苯甲酸 ( 2 ) 和异氰化物3的三组分帕塞里尼反应产生叠氮化物中间体4，其依次用三苯基膦、异氰酸酯 (或 CS 2 ) 和仲胺处理得到多取代的 3,4 -二氢喹唑啉8和 4 H -3,1-苯并噻嗪11通过连续的 Passerini/Staudinger/aza-Wittig/加成/亲核取代反应获得良好的总产率。