阿扎-基甲基促进了由Azabicyclo[1.1.0]butanes的压力释放驱动的转化为功能化的阿丁素
Bandana Singh1, Pujan Sasmal2, Aaron Taites2
1Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, Lucknow 226014, India.
Organic letters
|October 25, 2024
概括
一种新的策略激活了azabicyclo[1.1.0]butanes用于N/C3-功能化,产生功能化的亚齐丁丁. 这些亚提丁可以转化为具有医学意义的印度林.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 亚扎比环[1.1.0] (ABBs) 是具有各种化学转化潜力的应变异环.
- 开发有效的方法来使ABB功能化对于访问新型分子支架至关重要.
研究的目的:
- 报告一个新的策略来激活azabicyclo[1.1.0]butanes (ABBs).
- 为了证明从ABBs中制备功能化亚丁的准备.
- 为了展示这些亚齐丁的转化为医学上相关的印林.
主要方法:
- 使用现场生成的aza-ortho-quinone methides激活ABBs.
- 使用六化醇 (HFIP) 促进反应.
- 压力释放驱动的ABB核心的N/C3功能化.
- 催化氨化用于印林合成.
主要成果:
- 成功制定了一项统一的激活ABB的战略.
- 从ABBs中有效地制备了功能化的亚齐丁丁.
- 合成的阿兹提丁因通过Pd催化胺化转化为印度林.
结论:
- 报告的方法提供了一条新的途径,从ABB中获得功能化亚兹提丁.
- 这种方法可以获得医学上相关的印林支架.
- 该战略强调了压力释放驱动的ABB功能化的实用性.
相关概念视频
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
2.9K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
2.9K
Preparation of 1° Amines: Azide Synthesis
3.9K
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...
3.9K
Nucleophilic Aromatic Substitution: Elimination–Addition
4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
5.8K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
5.8K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
17.8K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
17.8K
Radical Chain-Growth Polymerization: Overview
2.4K
Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
2.4K


