活性化されていないアニリンを酸化してN-アリルニトロイドを生成する
Tianning Deng1, Wrickban Mazumdar1, Russell L Ford1
1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
Journal of the American Chemical Society
|February 12, 2020
まとめ
新しい方法は,2代入のアニリンを低温で酸化して,N-アリルニトロイド中間物質を生成する. これは,スパイロサイクルの3Hインドルとベンザゼピノンを含む機能化されたN-ヘテロサイクルの合成を可能にします.
科学分野:
- 有機化学
- 合成化学
- ヘテロサイクル化学
背景:
- N-ヘテロサイクルの効率的な合成経路の開発は,医薬品化学と材料科学において極めて重要です.
- 伝統的な方法は,しばしば厳しい条件または保護グループを必要とし,基板の範囲と効率を制限します.
研究 の 目的:
- 2 置換アニリンのための,低温,保護グループフリー酸化方法を開発する.
- 生成されたN-アリルニトロイド中間物質を機能化されたN-ヘテロサイクルの構築に使用する.
主な方法:
- フェニリオジン (III) ビス (トリフオロアセテート) (PIFA) をトリフオロアセチウム酸またはスカンジウムトリフラート (Sc (OTf)) を使用した2代入アニリンの酸化.
- C-NArとC-C結合形成のために,現地で生成されたN-アリルニトロイド中間物質を使用する.
主要な成果:
- スパイロサイクリックとバイサイクリック3Hインドールとベンザゼピノンの成功合成
- 選択的なC-NArとC-C結合形成経路の実証
- 酸化過程における選択性を制御する要因の特定.
結論:
- 開発された方法は,穏やかな条件下で多様なN-ヘテロサイクルへの簡単で効率的な経路を提供します.
- N-アリルナイトレノイドの中間体は,複雑な分子構造を構築するための多用途の反応性を示す.
- このアプローチは,価値ある3Hインドルとベンザゼピノンを入手するための合成ツールボックスを拡張します.
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