功能化纳夫托[2,1-d]oxazoles的合成的迪亚佐策略
Timur O Zanakhov1, Ekaterina E Galenko1, Mikhail S Novikov1
1Saint Petersburg State University, Institute of Chemistry, 7/9 Universitetskaya Naberezhnaya, St. Petersburg 199034, Russia.
The Journal of organic chemistry
|July 22, 2025
概括
通过阿齐林扩张的新氧化合成可以获得纳夫托[2,1-d]氧化. 这些化合物允许易于修饰并进一步转化为新型的[7,8]异[5,6-d]氧-7-one衍生物.
科学领域:
- 有机合成 有机合成
- 异环化学 异环化学
- 催化剂是一种催化剂.
背景情况:
- 阿齐林化学为构建复杂的异环系统提供了独特的途径.
- Rh (II) 催化反应是C-H功能化和碳素插入的强大工具.
- 纳夫托[2,1-d]奥克萨支架对药物化学和材料科学有兴趣.
研究的目的:
- 开发一种新型的合成途径,以 (oxazol-4-yl) 替代2-diazo-1,3-dicarbonyl化合物.
- 探索这些二氧化化合物的Rh (II) 催化转化到纳夫托[2,1-d]oxazole.
- 为了研究纳夫托[2,1-d]oxazole核心的后续功能化和进一步衍生.
主要方法:
- 使用三酸乙 (TFAA) 的阿齐林环扩张.
- ((II) 催化的金属碳化合物的分子内C-H插入.
- 基基团的化,然后是催化交叉合反应.
- 索诺加希拉合产品的易斯酸促进循环.
主要成果:
- 有效合成基二-子三-氧-5-/二-三甲基) 醇四-) 酸盐.
- 通过Rh (II) 催化,选择性形成4-氧纳[2,1-d]oxazole-5-carboxylic .
- 通过三和交叉合,轻松修改4位置换剂.
- 获得新型的7H-[7,8]异烯[5,6-d]氧-7-衍生物.
结论:
- 已经建立了一个用于构建功能化纳夫托[2,1-d]oxazoles的多功能合成策略.
- 开发的方法允许纳夫托[2,1-d]奥克萨核心的晚期多样化.
- 新的异环骨的合成扩大了药物发现和材料开发的化学空间.
更多相关视频
相关概念视频
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
3.1K
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...
3.1K
Diazonium Group Substitution: –OH and –H
2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.0K
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...
2.0K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
4.0K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.0K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.2K
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,...
2.2K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.8K


