一个快速,温和和直接的途径,从硫胺胺到硫胺化物
Padma Priya V R1, Antony Haritha Mercy A1, Natarajan K1
1Department of Chemistry, National Institute of Technology, Tiruchirappalli, Tamilnadu 620015, India.
The Journal of organic chemistry
|October 31, 2024
概括
这项研究引入了一种快速而温和的方法,可以从硫胺酸中合成硫胺基化物[S(VI][S(II) ]. 这种新的协议可以直接将硫胺转化为有价值的硫胺基化物化合物.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 硫胺 [S(II) ] 是有机合成中的多功能前体.
- 从硫胺酸中直接合成硫胺基化物[S(VI]是具有挑战性和未被充分研究的.
- 现有的获取硫化合物的方法往往需要苛刻的条件或多步骤的程序.
研究的目的:
- 开发一种快速和温和的协议,用于从硫胺基中直接合成硫胺基化物[S(VI] [S(II) ].
- 探索该协议在合成功能化硫胺基化物 (包括从药物分子中衍生出来的化物) 的实用性.
- 为了研究硫胺基化物后续转化为硫胺基化物.
主要方法:
- 硫胺基[S(II]与N-糖胺基 (NCS),水和四甲基化物 (TBAF) 在酸中发生的反应.
- 使用水用于SO键形成和TBAF作为化物来源.
- 使用AlCl3将硫胺基化物转化为硫胺基.
主要成果:
- 一个直接的,快速的 (在5分钟内) 和温和的协议,用于合成硫胺基化物[S(VI]从硫胺基[S(II]建立.
- 该协议成功地合成了来自卡巴马西和莱维拉cetam等药物分子的硫胺基化物.
- 使用AlCl3.3,硫胺基化物被有效地转化为硫胺基.
结论:
- 这项工作介绍了首次报告的从S(II) - 硫胺基中直接合成硫胺基化物[S(VI]的情况.
- 开发的协议提供了一种高效和多功能途径,以获得有价值的硫化合物.
- 该方法对药物衍生分子的适用性突显了其在药物化学和药物发现方面的潜力.
更多相关视频
相关概念视频
Preparation and Reactions of Sulfides
4.7K
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.
4.7K
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
Amines to Sulfonamides: The Hinsberg Test
3.2K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
3.2K
Electrophilic Aromatic Substitution: Sulfonation of Benzene
5.8K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
5.8K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
5.8K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
5.8K
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
![Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F2755.jpg&w=3840&q=50)

