通过亚和环合素中间体合成硫胺
Xianda Wu1, Minghong Chen1, Fu-Sheng He1
1School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, Jiaojiang 318000, Zhejiang, China.
Organic letters
|July 5, 2023
概括
一种新的无金属方法有效地利用氨酸和环氨酸前体从硫胺中合成硫胺. 这种方法涉及独特的S-C键形成,产生多种不同的硫胺,并使进一步转化为硫胺成为可能.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 硫胺是多用途的硫化合物,在药物化学和材料科学中具有重要的应用.
- 现有的合成路线通常需要恶劣的条件,昂贵的催化剂,或缺乏广泛的基质范围.
研究的目的:
- 开发一种高效的,无金属的合成策略,以获取各种各样的硫胺.
- 探索一种涉及S-C键形成的新反应途径.
- 为了证明合成的硫胺的可扩展性和进一步的效用.
主要方法:
- 硫胺的反应与阿林和环素前体.
- 没有金属的反应条件.
- 硫胺产品的净化和表征.
主要成果:
- 在中等到良好的产量中成功合成各种硫胺.
- 在S-C键形成中表现出卓越的化学选择性.
- 协议的可扩展性到格拉姆尺度合成.
- 合成的硫胺转化为有价值的硫胺.
结论:
- 开发的无金属协议提供了一条实用而高效的硫胺的途径.
- 新的S-C键形成机制扩大了合成的可能性.
- 该协议的可扩展性和适用于硫胺合成的应用性突显了其潜力.
更多相关视频
相关概念视频
Preparation and Reactions of Sulfides
4.9K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.9K
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
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: 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
Preparation of Alkynes: Alkylation Reaction
10.3K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
10.3K
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


