2-(4-bromophenyl)imidazo[1,2-a]pyridin-3-amine | 421596-09-0

• 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-(4-bromophenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 421596-09-0
• 化学式: C₁₃H₁₀BrN₃
• 分子量: 288.147
• InChiKey: LAAXWJGVLMSJMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)imidazo[1,2-a]pyridin-3-amine 、 丁烯-2-醛 在 10% palladium on active carbon 作用下， 以 邻二氯苯 为溶剂， 反应 30.0h， 以42%的产率得到1-(4-Bromo-phenyl)-6-methyl-6,7-dihydro-2,9,9b-triaza-benzo[cd]azulene
  参考文献：
  名称：

  Aminoimidazo[1,2-a]pyridines: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines

  摘要：

  In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo [1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (+/-)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and alpha,beta-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01141-3
• 作为产物：
  描述：

  2-(4-bromophenyl)-N-(tert-butyl)imidazo[1,2-a]pyridin-3-amine 在 tetrafluorohydroboric acid 作用下， 以 水 、 正丁醇 为溶剂， 反应 0.33h， 生成 2-(4-bromophenyl)imidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Towards molecular diversity: dealkylation of tert-butyl amine in Ugi-type multicomponent reaction product establishes tert-butyl isocyanide as a useful convertible isonitrile

  摘要：

  随着一种新型微波辅助单锅联产去叔丁基化的开发，在Ugi型多组分反应生成物中，叔丁基异氰酸酯作为一种有用的可转化异腈首次被探讨，从而获得了制药上重要的多环氮融合咪唑杂环的分子多样性。

  DOI：

  10.1039/c0ob00022a

文献信息

• Electrochemical primary amination of imidazopyridines with azidotrimethylsilane under mild conditions
  作者：Yan Zhu、Qiao Chu、Heng Li、Ping Liu、Peipei Sun

  DOI：10.1039/d2gc03703c

  日期：——

  A straightforward protocol involved electrochemical primary amination of imidazopyridines under mild conditions was described, in which TMSN₃ was used as the nitrogen source and a trace amount of H₂O was used as the hydrogen source.

  描述了一种简单的协议，涉及在温和条件下电化学原位氨基化咪唑吡啶，其中使用TMSN3作为氮源，微量的H2O作为氢源。
• HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING ELEMENT USING SAME
  申请人：Heesung Material Ltd.

  公开号：EP3214085A2

  公开（公告）日：2017-09-06

  The present specification relates to a novel hetero-cyclic compound and an organic light emitting device using the same.

  本说明书涉及一种新型杂环化合物和使用该化合物的有机发光器件。
• Aminoimidazo[1,2-a]pyridines: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines
  作者：Jean M Chezal、Emmanuel Moreau、Olivier Chavignon、Vincent Gaumet、Jacques Métin、Yves Blache、Anna Diez、Xavier Fradera、Javier Luque、Jean C Teulade

  DOI：10.1016/s0040-4020(01)01141-3

  日期：2002.1

  In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo [1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (+/-)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and alpha,beta-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results. (C) 2002 Published by Elsevier Science Ltd.
• Towards molecular diversity: dealkylation of tert-butyl amine in Ugi-type multicomponent reaction product establishes tert-butyl isocyanide as a useful convertible isonitrile
  作者：Sankar K. Guchhait、Chetna Madaan

  DOI：10.1039/c0ob00022a

  日期：——

  With the development of a novel microwave-assisted one-pot tandem de-tert-butylation of tert-butyl amine in an Ugi-type multicomponent reaction product, tert-butyl isocyanide as a useful convertible isonitrile has been explored for the first time affording access to molecular diversity of pharmaceutically-important polycyclic N-fused imidazo-heterocycles.

  随着一种新型微波辅助单锅联产去叔丁基化的开发，在Ugi型多组分反应生成物中，叔丁基异氰酸酯作为一种有用的可转化异腈首次被探讨，从而获得了制药上重要的多环氮融合咪唑杂环的分子多样性。