オレフィンとアジリジンの酸化性サイクロアミネーションは,飽和した窒素を含むヘテロサイクルのための汎用的な経路としてアジリジンを用います
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Journal of the American Chemical Society
|November 20, 2003
まとめ
新しいバイサイクリックアジリジンは,NHアジリジンとN-ブロモスクシニミドを用いて酸化性サイクロアミネーションによって合成されます. これらの多用途な化合物は,多様なピロリジンおよびピペリジンヘテロサイクルの合成経路を提供します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 合成化学 合成化学とは
背景:
- アジリジンは,重要な合成的有用性を持つストレインされた3つ組のヘテロサイクルです.
- バイサイクルアジリジンは,ユニークな構造的特徴と反応性を備えています.
- 複雑なアジリジン・スキャフォルドを合成するための効率的な方法の開発は極めて重要です.
研究 の 目的:
- 高度反応性のある[5,3]および[6,3]バイサイクルアジリジンを製造するための簡単な方法を開発する.
- これらの新種のバイサイクルアジリジンの合成的有用性を探求する.
- エキソメチレンバイサイクルアジリジンの安定性と反応性を調査する.
主な方法:
- NHアジリジンとN-ブロモスクシニミドを用いたオレフィンの分子内酸化サイクロアミネーション.
- 合成されたバイサイクルアジリジン製品の特徴.
- ピロリジンおよびピペリジン誘導体を形成する後の反応の探索.
主要な成果:
- [5,3] と [6,3] バイサイクルアジリジンの成功的かつ効率的な製剤.
- 驚くほど安定したエクソメチレンバイサイクルアジリジンの分離.
- 様々なピロリジンおよびピペリジンヘテロサイクルへの汎用的な合成アクセスの実証.
結論:
- 内分子酸化サイクロアミネーションは,バイサイクルアジリジン合成の効果的な戦略です.
- 合成されたバイサイクルのアジリジンは,ヘテロサイクルの合成のための貴重な中間物質として機能します.
- この方法論は,窒素を含むヘテロサイクルの構築のためのツールキットを拡張します.
関連する概念動画
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02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
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Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Overview
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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 peroxy acids to...
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 peroxy acids to...
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Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...