使用triazolobenzodiazepine作为各种类型的Joullié-Ugi反应中的循环 imine
Mohammad Taghi Nazeri1, Maryam Ghasemi1, Masoomeh Ahmadi1
1Department of Organic Chemistry, Shahid Beheshti University, Daneshjou Boulevard, Tehran, 1983969411, Iran.
The Journal of organic chemistry
|September 11, 2023
概括
通过多组分反应合成了新的三二二胺化合物. 这些反应,包括Joullié-Ugi和伪Joullié-Ugi变体,在温和条件下提供有效的路径,以获得新的化学结构.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 三二二胺是一种具有潜在生物活性的异环化合物.
- 多元组分反应 (MCR) 为合成复杂分子提供了高效的途径.
研究的目的:
- 探索三二二胺作为Joullié-Ugi和修改的Ugi反应中的循环 imine的实用性.
- 合成新型的三醇二胺衍生物和化醇系统.
主要方法:
- 利用了涉及循环 imines,异化物和碳酸/水/TMSN3.3 的三组分Joullié-Ugi反应.
- 在没有催化剂的条件下,采用了伪朱利埃-乌吉反应与循环 imines,异化物和乙烯基碳酸盐.
主要成果:
- 在高产量中合成了三种新家族的triazolobenzodiazepine-carboxamide和triazolobenzodiazepine-tetrazole产品.
- 通过经过修改的Ugi反应开发了一种新型的无催化剂合成的 triazolobenzodiazepine-fused pyrroles.
- 在温和条件下,在各种Ugi型反应中证明了 triazolobenzodiazepine 的广泛适用性.
结论:
- 三二二胺胺是合成多种异环基架的多功能构件.
- 开发的基于Ugi的策略为新型化学实体提供了高效和温和的途径.
- 机理学研究揭示了一个意想不到的途径,用于形成三二二胺融合的pyrroles.
相关概念视频
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
3.2K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
3.5K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.5K
Preparation of 1° Amines: Azide Synthesis
4.0K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.0K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Aldehydes and Ketones with Amines: Imine Formation Mechanism
5.7K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
5.7K


