二次アミンの直接的な窒素除去による骨格編集
Sean H Kennedy1, Balu D Dherange1, Kathleen J Berger1
1Department of Chemistry, University of Chicago, Chicago, IL, USA.
Nature
|May 13, 2021
まとめ
化学者は有機分子から窒素を取り除く 新しい反応を開発し 炭素と炭素の結合を可能にしました この方法は複雑な分子合成と生物活性化合物の骨格編集を容易にする.
科学分野:
- 合成有機化学
- カタリシス
- 反応方法論
背景:
- 合成化学は 単純な前体から複雑な分子を作ろうとする.
- 分子構造の精密な操作は 限られていて 新しい化学空間へのアクセスを妨げています
- 炭素-炭素結合を形成する 新しい反応の開発は 分子構造に不可欠です
研究 の 目的:
- 有機分子から窒素を除去する 新しい反応を報告する
- 窒素駆出による分子内炭素結合を可能にする.
- 複雑な有機分子の骨格編集と合成のための新しい戦略を提供する.
主な方法:
- N-ピヴァロイロキシ-N-アルコキシアミドを使用し,アノメリックアミドのサブクラスです.
- 二次アリファティックアミンの分子間活性化の研究.
- イソジアゼンの中間物質とダイラジカルを含むメカニズム的研究を実施した.
主要な成果:
- 有機分子から窒素を効果的に除去する反応を開発した.
- ダイラジカルカップリングによる分子内炭素結合形成.
- 幅広い機能群への耐性が実証されている.
- 生物活性化合物の合成と編集に 反応を成功させた
結論:
- 報告された反応は,窒素挤出によるC−C結合形成のための新しい方法を提供します.
- この変換は有機化学における骨格の編集と合成のための多用途なツールを提供します.
- この反応の広範な適用は,複雑で生物活性な分子のための合成の可能性を拡大します.
さらに関連する動画
関連する概念動画
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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01:30Preparation of Amines: Alkylation of Ammonia and Amines
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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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01:38Preparation of Amines: Reductive Amination of Aldehydes and Ketones
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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01:28Preparation of 1° Amines: Gabriel Synthesis
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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...
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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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01:07Amines: Introduction
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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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