铜促进的C5选择性化8-氨基氨酸胺基与基化物
Changdong Shao1, Chen Ma1, Li Li1
1Jiangsu Provincial Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an, 223300, Jiangsu, China.
Beilstein journal of organic chemistry
|January 31, 2024
概括
一种新方法有效地利用铜促进化合成C5-化8-氨基氨酸胺基. 这种实用方法为各种基板提供了高选择性和产量.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
背景情况:
- 8-氨基氨酸胺是药物化学中的关键支架.
- 选择性功能衍生物的高效合成对于药物发现至关重要.
研究的目的:
- 开发一种实用且高效的方法,用于选择性C5化8-氨基诺氨基胺.
- 探索铜催化和基化物用于这种转化.
主要方法:
- 铜促进的选择性化8-氨基氨酸氨基胺.
- 使用活性化和非活性化基化物作为化剂.
- 在环境空气条件下在二甲基硫氧化物 (DMSO) 中进行的反应.
主要成果:
- 实现了C5-化8-氨基基诺林胺基的高效合成.
- 在C5位置证明了化出色的选择性.
- 在广泛的基板上获得了出色的产量.
- 反应在不需要外部氧化剂的情况下进行.
结论:
- 开发了一种新,高效和实用的铜催化方法,用于C5-化8-氨基诺氨基胺.
- 该方法为合成多种化8-氨基诺林衍生物提供了一种有价值的工具.
- 这种方法有助于在药物化学应用中进一步探索这些化合物.
相关概念视频
Radical Substitution: Allylic Bromination
5.1K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.1K
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
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
8.1K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
8.1K
Amines to Amides: Acylation of Amines
2.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.5K
Preparation of Amines: Alkylation of Ammonia and Amines
3.4K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.4K
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


![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)