パラジアム触媒によるアミド含有3,4-ジヒドロイソキノリン-1 ((2H) -オンの合成N-プロパルギラミド
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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。新しいパラジウム触媒反応は,N-プロパルギラミドとアミンから3,4-ジヒドロアイソキノリン-1 ((2H) -オンを含む構造を効率的に生成します. ベンゼン-1,3,5-トリルトリフォームートは,この合成のための安全な一酸化炭素源として機能します.
科学分野
- 有機化学
- カタリシス
- 合成方法論
背景
- 3,4-ジヒドロアイソキノリン-1(2H) - 1のエスカファードは,医薬品で一般的です.
- 機能化されたイソキノリノンのための効率的な合成経路は非常に求められています.
研究 の 目的
- 3,4-ジヒドロイソキノリン-1 ((2H) - 1 誘導体を合成するための新しいパラジアム触媒法を開発する.
- アイソキノリノンの核構造にアミドユニットを組み込む.
主な方法
- パラジウム触媒による循環と炭化反応.
- N-プロパルギラミドとアミンを原料として利用した.
- 炭素一酸化物源としてベンゼン-1,3,5-トリルトリフォーム酸 (TFBen) を使用した.
主要な成果
- アミドを含む3,4-ジヒドロアイソキノリン-1 (((2H) - 1の様々な配列を成功裏に合成した.
- 標的化合物の高収量を達成しました.
- 安全で便利なCO代用体としてのTFBenの有用性を実証した.
結論
- 開発された方法は,機能化されたイソキノリノンのための簡単な経路を提供します.
- このアプローチは医薬品化学と薬剤開発に 価値あるツールとなります
- TFBenの使用は,カーボニレーションプロセスの安全性と実用性を高めます.
関連する概念動画
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In 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...
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...
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...