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绿色电合成 bis (indolyl) 甲衍生物在深层欧性溶剂中的绿色电合成
Mina E Adly1, Amr M Mahmoud2, Hala B El-Nassan3
1Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Cairo University, 33 Kasr El-Aini Street, Cairo, 11562, Egypt.
BMC chemistry
|July 27, 2024
概括
开发了一种新的绿色合成方法,用于 bis (indolyl) 甲衍生物,使用电化学在深层环氧溶剂中. 这种高效的方法提供了温和的条件,短的反应时间和高产的各种替代芳香性化物.
科学领域:
- 绿色化学 绿色化学
- 有机合成 有机合成
- 电化学 电化学 电化学
背景情况:
- 传统的二甲衍生物合成通常涉及恶劣的条件和危险的溶剂.
- 深度浸泡溶剂 (DES) 为传统溶剂和电解质提供了可持续和环保的替代品.
- 电化学合成为有机转化提供了一种可控和高效的方法.
研究的目的:
- 开发一种新的,绿色的,高效的电化学方法,用于合成二甲衍生物.
- 探索使用深度环氧溶剂作为电化学合成的反应介质.
- 优化反应参数并研究开发方法的范围.
主要方法:
- 在合成过程中采用了电化学双糖化反应.
- 作为反应介质,使用了深度浸泡溶剂,特别是乙烯基醇/胆化物 (2:1比),作为反应介质.
- 石墨和电极分别作为阴极和阳极.
- 系统地研究了反应条件,包括时间,电流,溶剂和电极材料.
主要成果:
- 使用乙烯基醇/胆化物,最佳反应条件为80°C,持续45分钟.
- 通过使用广泛的替代芳香性化物 (电子捐赠和电子提取) 实现了高产品产量.
- 电化学方法在DES中表现出比传统加热更高的效率,在更短的时间内产生更高的产品量.
- 反应机制被提出并得到循环电压测量研究的支持.
结论:
- 成功开发了一种新的,绿色和高效的电化学方法,用于在深层环氧溶剂中合成二甲衍生物.
- 这种方法提供了显著的优势,包括温和的条件,短的反应时间,高产量和广泛的基质范围.
- 在DES中使用电化学方法是合成有价值的双乙烯 (indolyl) 甲化合物的有希望和可持续的替代方案.
相关概念视频
01:17Thermal Electrocyclic Reactions: Stereochemistry
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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01:26Thermal and Photochemical Electrocyclic Reactions: Overview
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
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Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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01:26Photochemical Electrocyclic Reactions: Stereochemistry
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
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