构造的pyrazolo[1,5-a]pyrimidines和pyrimido[1,2-b]indazoles与碳化作为一个alkyne来源的化物
Xinjie You1, Botao Wang1, Fei Wen2
1College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. China. lizheng@nwnu.edu.cn.
Organic & biomolecular chemistry
|July 2, 2024
概括
这项研究引入了一种更安全,更有效的方法来合成pyrazolo[1,5-a]pyrimidines和pyrimido[1,2-b]indazoles. 碳化取代了危险的乙,简化了过程,并使用了易于获得的材料.
科学领域:
- 有机合成 有机合成
- 异环化学 异环化学
- 绿色化学 绿色化学
背景情况:
- 传统的合成pyrazolo[1,5-a]pyrimidines和pyrimido[1,2-b]indazoles经常涉及危险的试剂,如气态乙.
- 开发更安全,更容易获得的合成途径对于在药物化学和材料科学领域的更广泛应用至关重要.
研究的目的:
- 开发一种高效,更安全的合成5-arylpyrazolo[1,5-a]pyrimidines和2-arylpyrimido[1,2-b]indazoles的方法.
- 在这些异环合成中,利用碳化作为气态乙的固体,安全的替代品.
- 建立一个具有广泛的功能组耐受性和可扩展性的多功能协议.
主要方法:
- 皮拉-3-胺或因达-3-胺与 (异味) 芳香性化物和碳化的反应.
- 铜介导循环化反应. 铜介导循环化反应.
- 反应条件的优化,包括溶剂,温度和催化剂负载.
主要成果:
- 成功合成了各种5-arylpyrazolo[1,5-a]pyrimidines和2-arylpyrimido[1,2-b]indazoles的成功合成.
- 碳化作为有效和安全的固体基因来源的证明.
- 该协议表现出广泛的功能组容忍度,并允许简单的处理程序.
- 反应的可扩展性得到了证实,直到格拉姆尺度合成.
结论:
- 开发了一种新,高效和安全的合成方法来构建重要的异环基架.
- 碳化的使用比传统的乙来源具有显著的优势,提高了安全性和实用性.
- 该协议可以进行大规模合成,这使得它对工业应用具有价值.
相关概念视频
01:22Preparation 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
01:28Preparation of 1° Amines: Gabriel Synthesis
3.5K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.5K
01:20Diazonium 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
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
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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.
2.1K
01:26Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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01:29Preparation of Amides
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.0K