ethyl 2-amino-6-fluoro-1H-indole-3-carboxylate | 365547-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 2-amino-6-fluoro-1H-indole-3-carboxylate
• CAS: 365547-79-1
• 化学式: C₁₁H₁₁FN₂O₂
• 分子量: 222.219
• InChiKey: YLBOVYZYMANSQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-6-fluoro-1H-indole-3-carboxylate 、 2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde 在 ytterbium(III) triflate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以51%的产率得到10-fluoro-7-phenyl-6,8-dihydrochromeno[3',4':5,6]pyrido[3,2-b]indole
  参考文献：
  名称：

  Lewis-Acid-Catalyzed Decarboxylative Annulation of 2-Aminoindole-3-Carboxylate with Ynals Involving [3 + 2] Spirocycloaddition and 2,3-Aza Migration

  摘要：

  2-Aminoindole-3-carboxylates undergo a Lewis-acid-catalyzed decarboxylative annulation with ynals to afford dihydro-chromeno-fused delta-carbolines through a 2,3-aza migration, via a spirocyclic intermediate generated from an initial [3 + 2] spirocycloaddition. Bronsted acid interference changes the path from a [3 + 2] to a [4 + 2] addition. 2-Aminoindoles without an ester functional group at C3 underwent a different condensation, followed by hetero-Diels Alder reaction to generate chromeno-fused alpha-carbolines.

  DOI：

  10.1021/acs.orglett.9b04626

文献信息

• Diversity-Oriented Synthesis of Polycyclic Indoles: Brønsted or Lewis Acid Catalyzed Three-Component Reaction for the Synthesis of α-Carbolines and Pyrimidoindoles
  作者：Rajesh K. Arigela、Ravi Kumar、Srinivas Samala、Sahaj Gupta、Bijoy Kundu

  DOI：10.1002/ejoc.201402633

  日期：2014.9

  diversity-oriented synthesis of pyrido- and pyrimido-indoles from an acid-catalyzed three component (3C) reaction involving ethyl 2-amino-1H-indole-3-carboxylates, arylaldehydes, and terminal alkynes. In the presence of a Bronsted acid such as trifluoroacetic acid (TFA), the 3C reaction furnished a mixture of pyrido- and pyrimido-indoles, whereas when catalyzed by Yb(OTf)3 as a Lewis acid, pyrimidoindoles

  我们报告了从涉及 2-氨基-1H-吲哚-3-羧酸乙酯、芳醛和末端炔烃的酸催化三组分 (3C) 反应中合成吡啶和嘧啶并吲哚的多样性。在布朗斯台德酸如三氟乙酸 (TFA) 的存在下，3C 反应提供了吡啶和嘧啶并吲哚的混合物，而当由 Yb(OTf)3 作为路易斯酸催化时，得到嘧啶吲哚作为单一产物. 这些发现证明了通过改变酸催化剂来控制反应产物的能力。TFA 催化的 3C 反应的显着特征是炔丙胺形成后在一个锅中遵循两种不同的途径。
• 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.
• Lewis-Acid-Catalyzed Decarboxylative Annulation of 2-Aminoindole-3-Carboxylate with Ynals Involving [3 + 2] Spirocycloaddition and 2,3-Aza Migration
  作者：Manda Rajesh、Ravi Kumar、Surendra Puri、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1021/acs.orglett.9b04626

  日期：2020.2.7

  2-Aminoindole-3-carboxylates undergo a Lewis-acid-catalyzed decarboxylative annulation with ynals to afford dihydro-chromeno-fused delta-carbolines through a 2,3-aza migration, via a spirocyclic intermediate generated from an initial [3 + 2] spirocycloaddition. Bronsted acid interference changes the path from a [3 + 2] to a [4 + 2] addition. 2-Aminoindoles without an ester functional group at C3 underwent a different condensation, followed by hetero-Diels Alder reaction to generate chromeno-fused alpha-carbolines.