ethyl 2-(4-methoxyphenyl)-4-phenylpyrimido[1,2-a]indole-10-carboxylate | 1324007-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 2-(4-methoxyphenyl)-4-phenylpyrimido[1,2-a]indole-10-carboxylate
• 英文别名: Ethyl 2-(4-methoxyphenyl)-4-phenylpyrimido[1,2-a]indole-10-carboxylate
• CAS: 1324007-11-5
• 化学式: C₂₇H₂₂N₂O₃
• 分子量: 422.483
• InChiKey: YIQHUIHFCUAGBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基吲哚-3-羧酸乙酯 、 1-(4-甲氧基-苯基)-3-苯基-propyn酮 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以70%的产率得到ethyl 2-(4-methoxyphenyl)-4-phenylpyrimido[1,2-a]indole-10-carboxylate
  参考文献：
  名称：

  Temperature-Gradient-Directed NMR Monitoring of a [3 + 3]-Cyclocondensation Reaction Between Alkynone and Ethyl 2-Amino-1H-indole-3-carboxylate Toward the Synthesis of Pyrimido[1,2-a]indole Catalyzed by Cs₂CO₃

  摘要：

  We describe a NMR strategy to resolve temperature-gradient-monitored real-time chemical reaction involving a [3+3]-cyclocondensation reaction between alkynone and ethyl 2-amino-1H-indole-3-carboxylate toward the synthesis of pyrimido[1,2-a]indole catalyzed by Cs2CO3. The in situ NMR study clearly indicates that the reactant undergoes [3+3]-cyclocondensation reaction through a concerted mechanism, resulting in the product formation. The detailed NMR spectroscopic data led to the optimization of the reaction conditions and quantitative analysis of the product accurately and efficiently. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.687423

文献信息

• Three-component tandem reaction involving acid chlorides, terminal alkynes, and ethyl 2-amino-1H-indole-3-carboxylates: synthesis of highly diversified pyrimido[1,2-a]indoles via sequential Sonogashira and [3+3] cyclocondensation reactions
  作者：Sahaj Gupta、Sudhir K. Sharma、Anil K. Mandadapu、Harsh M. Gauniyal、Bijoy Kundu

  DOI：10.1016/j.tetlet.2011.06.021

  日期：2011.8

  A simple, highly efficient three-component reaction involving acid chlorides, terminal alkynes, and ethyl 2-amino-1H-indole-3-carboxylates, for the synthesis of highly diversified pyrimido[1,2-a]indoles has been described. The salient feature of the reaction involves sequential Sonogashira and [3+3] cyclocondensation reactions. (C) 2011 Elsevier Ltd. All rights reserved.
• Temperature-Gradient-Directed NMR Monitoring of a [3 + 3]-Cyclocondensation Reaction Between Alkynone and Ethyl 2-Amino-1<i>H</i>-indole-3-carboxylate Toward the Synthesis of Pyrimido[1,2-<i>a</i>]indole Catalyzed by Cs₂CO₃
  作者：Harsh M. Gauniyal、Sahaj Gupta、Sudhir K. Sharma、Usha Bajpai

  DOI：10.1080/00397911.2012.687423

  日期：2013.8.3

  We describe a NMR strategy to resolve temperature-gradient-monitored real-time chemical reaction involving a [3+3]-cyclocondensation reaction between alkynone and ethyl 2-amino-1H-indole-3-carboxylate toward the synthesis of pyrimido[1,2-a]indole catalyzed by Cs2CO3. The in situ NMR study clearly indicates that the reactant undergoes [3+3]-cyclocondensation reaction through a concerted mechanism, resulting in the product formation. The detailed NMR spectroscopic data led to the optimization of the reaction conditions and quantitative analysis of the product accurately and efficiently. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.