アザ・ディエノフィルとしてのケテニミン
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PubMedで要約を見る
まとめ
この要約は機械生成です。N-アリルケテニミンは強力なアザ-ディエノフィルとして機能し,フラン派生体との選択的なサイクル添加を可能にします. この反応は,酸素化されたピリドンをコンバージェント,リドックス中性経路で効率的に生成する.
科学分野
- 有機化学
- 合成化学
背景
- N- アリルケテニミンはその反応性で知られている.
- アザディオニオフィルは,サイクロアディション反応において極めて重要です.
研究 の 目的
- N-アリルケテニミンのサイクロアディション反応を探求する.
- 酸素化されたピリドン誘導体を合成する方法を開発する.
- 他のダイノフィールと比較してN-アリルケテニミンの反応性を調査する.
主な方法
- N-アリルケテニミンと2,5-ビス (シリロキシ) フランを用いた分子間サイクル添加.
- 触媒の存在下での加熱反応
- 実験と計算による研究
- アザ・ディエノフィルの派生
- 一鍋の多成分反応です
主要な成果
- 高度な周回,地域,化学,およびダイアステレオ選択性が得られた.
- 自発的なC-O分裂は酸素化されたピリドンの誘導体をもたらした.
- N- アリルケテニミンは,歪んだ移行状態が少ないため,イミノディーノフィールよりも高い反応性を示した.
- イソシアネートとサイクルケテンミンの同等の開発.
- ピリドンとピランを融合させるための3つのコンポーネントのアプローチが確立されました.
結論
- N-アリルケテニミンは,酸素化されたピリドンを合成する非常に効果的なアザ-ディエノフィルです.
- 反応経路は収束し,酸化還元中性である.
- N-アリルケテニミンの反応性の向上は,合成戦略において利点をもたらします.
関連する概念動画
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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...
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Figure 1. Common names for functionalized anilines based on substitution.
For the systematic...
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...
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
Figure 1. The mechanism of the diazotization reaction of primary amines.
As illustrated in Figure 1, in the...
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Figure 1.
A primary arylamine attacks the nitrosonium ion to form an...