新型异尿-乙烯-绑定-皮佩拉衍生物的单四组分合成
Fatima Hajizadeh1, Mohammad M Mojtahedi1, M Saeed Abaee1
1Organic Chemistry Department, Chemistry and Chemical Engineering Research Center of Iran P.O. Box 14335-186 Tehran Iran mojtahedi@ccerci.ac.ir.
RSC advances
|November 9, 2023
概括
一种新型的无金属合成有效地产生与异尿基相关联的皮佩拉衍生物. 这种四组分反应使用1,4-diazabicyclo[2.2.2]octane (DABCO) 盐,并提供了一条通往复杂分子的多功能途径.
科学领域:
- 有机合成 有机合成
- 药用化学 医学化学
- 异环化学 异环化学
背景情况:
- 皮佩拉衍生物是药物化学中的关键支架.
- 异尿素部分存在于各种生物活性化合物中.
- 有效的合成路径可用于绑定的piperzine-isothiourea结构是可取的.
研究的目的:
- 开发一种新的,高效的,不含金属的合成策略,用于异尿素-乙烯-绑定-piperazine衍生物.
- 探索一个四组分反应,涉及1,4-diazabicyclo[2.2.2]octane (DABCO) 盐,氨基和化 (PITC).
主要方法:
- 在现场生成DABCO盐,通过DABCO与基化物反应.
- 一四组分反应,涉及DABCO盐,PITC和二次胺.
- 使用并行核添加路径,然后进行中间组合和C-N键裂解.
主要成果:
- 通过乙烯链接器成功合成了通过乙烯链接器连接到异urea 组的 piperazine 衍生物.
- 对于目标的异尿素-乙烯-绑定-皮佩拉化合物,取得了良好的高产.
- 在开发的协议中证明了对各种DABCO盐和二次胺的耐受性.
结论:
- 开发的四组分反应为合成异尿素-乙烯-绑定-皮佩拉衍生物提供了一个高效和无金属的途径.
- 该方法非常通用,可以容纳一系列的基板.
- 这种方法为获取具有潜在制药应用的新型异环化合物提供了有价值的工具.
相关概念视频
01:22Preparation of 1° Amines: Azide Synthesis
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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...
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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...
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