获取Pyrazolo[1,5-a]pyrimidinone Regioisomers 来自乙基化膜酸中的获取方法
1Department of Chemistry, Umeå University, SE 901 87 Umeå, Sweden.
Organic letters
|December 22, 2025
概括
研究人员开发了两种高效的方法来合成pyrazolo[1,5-a]pyrimidinones使用3-aminopyrazoles和乙烯酸Meldrum的酸. 反应条件允许在高产量中选择性合成pyrazolo[1,5-a]pyrimidin-5-ones或-7-ones.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 异环化学 异环化学
背景情况:
- 皮拉佐罗[1,5-a]胺是药物化学中的重要支架.
- 这些异循环的高效和区域选择性合成至关重要.
- 对于某些pyrazolo[1,5-a]pyrimidinone子类的以前的合成途径是有限的.
研究的目的:
- 开发新,高效和区域选择性方法来合成功能化的pyrazolo[1,5-a]pyrimidinones.
- 探索乙基化梅尔德鲁姆酸作为多功能构建块的实用性.
- 提供一个可靠的合成路径,以pyrazolo[1,5-a]pyrimidin-5-ones.
主要方法:
- 3-aminopyrazoles与乙基化梅尔德鲁姆酸的反应.
- 针对区域选择性的反应条件的优化.
- 合成产品的分离和表征.
主要成果:
- 为区域选择性合成建立了两种互补的方法.
- 实现了pyrazolo[1,5-a]pyrimidin-5-ones和pyrazolo[1,5-a]pyrimidin-7-ones的选择性形成.
- 对两种异构体都获得了高产量.
结论:
- 开发了一种可靠和高效的pyrazolo[1,5-a]pyrimidinone合成协议.
- 乙基化梅尔德鲁姆酸是区域选择性异环结构的有价值的合成物.
- 这些方法有助于生成生物相关的脚手架.
相关概念视频
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
3.6K
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.
3.6K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
4.0K
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...
4.0K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
2.8K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.8K
Preparation of 1° Amines: Azide Synthesis
4.5K
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...
4.5K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.8K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.8K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.6K
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,...
2.6K


![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)