N-アリラミドからリン酸化オキサゾリンを電気化学的に合成する
Jagadeesh Reddy Thondur1, Punith S Gowda1, Duddu S Sharada2
1Department of Chemistry, Indian Institute of Technology Hyderabad (IITH), Kandi, Sangareddy, Telangana 502285, India. gvsatya@chy.iith.ac.in.
まとめ
新しい電気化学的方法により,フェロセンの媒介を用いて酸化オキサゾリンを効率的に合成します. この緑のアプローチは 薬剤発見のための穏やかな条件と広い基板の範囲を提供します
科学分野:
- 有機化学
- 電気化学
- 薬剤化学
背景:
- リン酸化オクサゾリンは様々な用途を持つ有価なヘテロサイクル化合物である.
- 有機合成において効率的で持続可能な合成方法の開発は極めて重要です.
研究 の 目的:
- リン酸化オクサゾリンを合成するためのグリーンで効率的な電気化学的方法を開発する.
- 開発されたプロトコルの範囲と限界を探求する.
主な方法:
- デアリルフォスフィン酸化物によるN-アリラミドの電気化学サイクル.
- 恒定電流と温和な酸化物質のない条件下で未分割のセルセットアップを使用します.
主要な成果:
- 開発されたプロトコルは,一連のリン酸化オクサゾリンを成功裏に合成した.
- 各種のN-アリラミドの産量は中等から非常に良好であった.
- この方法は薬物の多様化に適していることが示された.
結論:
- フェロセーン媒介による電気化学循環は,リン酸化オクサゾリンへのグリーンで効率的な経路を提供します.
- この方法は,価値あるヘテロサイクルの化合物へのアクセスのための持続可能な代替手段を提供します.
- 薬剤の多様化におけるプロトコルの適用性は,医薬品化学におけるその可能性を強調しています.
関連する概念動画
Preparation of 1° Amines: Gabriel Synthesis
3.8K
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...
3.8K
Preparation of 1° Amines: Azide Synthesis
4.1K
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...
4.1K
Preparation of Epoxides
8.1K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
8.1K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.8K
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
3.5K
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.
3.5K
Acid-Catalyzed Ring-Opening of Epoxides
7.7K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.7K


![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)