5,6-dihydro[1,2,3]triazolo[5,1-a]isoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,6-dihydro[1,2,3]triazolo[5,1-a]isoquinoline
• 英文别名: 5,6-Dihydrotriazolo[5,1-a]isoquinoline
• 化学式: C₁₀H₉N₃
• 分子量: 171.202
• InChiKey: GXNQQBFIQBTZQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(o-iodophenyl)ethyl methanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 5,6-dihydro[1,2,3]triazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquino­lines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation­

  摘要：

  An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types.

  DOI：

  10.1055/s-0032-1316839

文献信息

• Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 1. Synthesis of cyclic amines
  作者：Clark、Hodgson、Goldsmith、Street

  DOI：10.1039/b108179a

  日期：2001.12.11

  Cyclic amines have been prepared in good yield by [2,3]-rearrangement of ammonium ylides produced by intramolecular reaction of copper carbenoids tethered to allylic amines. Copper(II) acetylacetonate is the optimum catalyst for carbenoid/ylide generation from the diazo ketone precursor, and reactions must be performed at elevated temperatures in order to obtain reasonable reaction rates and high yields. The reaction has been used to prepare five- to eight-membered cyclic amines. In cases where the substrate possesses a substituent on the tether connecting the diazo group to the allylic amine, tandem ylide formation and rearrangement delivers a high yield of the expected 2,5-dialkylpyrrolidinone or 2,6-dialkylpiperidinone, but low levels of diastereocontrol are obtained.Two new methods have been developed for the synthesis of diazo ketones containing a nucleophilic allylic amine substituent. The first method involves conjugate addition of allylic amines to unsaturated diazo ketones and is high yielding but of limited scope. The alternative general sequence involving nitrogen protection, α-diazo ketone formation, deprotection and allylation can be used to prepare the substrates required for intramolecular tandem ylide formation and rearrangement.

  循环胺通过铵亚胺的[2,3]-重排反应得到，铵亚胺是通过与烯基胺相连的铜羧肽的分子内反应生成的。铜(II)乙酰乙酮是从二氮酮前体生成羧肽/亚胺的最佳催化剂，反应必须在高温下进行，以获得合理的反应速率和高产率。该反应已用于合成五到八员环的循环胺。在底物具有连接二氮基与烯基胺的桥梁上的取代基的情况下，串联亚胺的形成和重排能高产率地生成预期的2,5-二烷基吡咯烷酮或2,6-二烷基哌啶酮，但获得的二面角控制水平较低。针对含有亲核烯基胺取代基的二氮酮的合成，开发了两种新方法。第一种方法涉及烯基胺对不饱和二氮酮的共轭加成，产率高但适用范围有限。另一种通用序列包括氮的保护、α-二氮酮的形成、去保护和烯基化，可用于合成所需的底物，以促进分子内的串联亚胺形成和重排反应。
• Triazolopyridines 20. Hydrogenation reactions
  作者：Belén Abarca、Rafael Ballesteros、Mostafá Elmasnouy

  DOI：10.1016/s0040-4020(99)00761-9

  日期：1999.10

  Hydrogenation reactions of some [1,2,3]triazolo[1,5-a]pyridines and their benzo derivatives, [1,2,3]-triazolo[1,5-a]quinoline and [1,2,3]triazolo[5,1-a]isoquinoline are studied. In general, the pyridine ring is more easily hydrogenated than the triazole or benzene rings.

  某些[1,2,3]三唑并[1,5- a ]吡啶及其苯并衍生物，[1,2,3]-三唑并[1,5- a ]喹啉和[1,2,3]的氢化反应研究了三唑并[5，1- a ]异喹啉。通常，吡啶环比三唑或苯环更容易氢化。
• US4075341A
  申请人：——

  公开号：US4075341A

  公开（公告）日：1978-02-21
• US4753722A
  申请人：——

  公开号：US4753722A

  公开（公告）日：1988-06-28
• USRE30456E
  申请人：——

  公开号：USRE30456E

  公开（公告）日：1980-12-23