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1-スルフォニル-1,2,3-トリアゾールをヘテロクミュレネスでトランスアンニュレーションする
Stepan Chuprakov1, Sen Wai Kwok, Valery V Fokin
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|March 13, 2013
まとめ
この研究は,1-メシル-1,2,3-トリアゾールを様々なイミダゾロンおよびチアゾールに変換する新しいRh(II) 触媒反応を示しています. このプロセスは,効率的なヘテロサイクルの合成のための反応性アザビニル金属カルベンを含む.
科学分野:
- 有機化学 オーガニック・ケミストリー
- カタリシス カタリシス カタリシス
- ヘテロサイクル化学 ヘテロサイクル化学
背景:
- 1,2,3-トリアゾールは,汎用性の高い合成中間物質です.
- ヘテロサイクルの合成のための効率的な方法の開発は,医薬品化学において極めて重要です.
- ロジウム ((II) 触媒反応は,分子変換のためのユニークな経路を提供します.
研究 の 目的:
- イミダゾロンとチアゾールの新しい合成経路を開発する.
- 1-メシル-1,2,3-トリアゾールの反応性について,窒素消去性変換で調べる.
- アザビニル金属炭基を含むメカニズムを調査する.
主な方法:
- ロジウム ((II) 触媒.
- 1-メシル-1,2,3-トリアゾールとイソシアネートおよびイソチオシアネートによる脱窒素反応.
- 提案された中間物質を含むメカニズム研究.
主要な成果:
- 1-メシル-1,2,3-トリアゾールをイミダゾロンおよびチアゾールに効率的に変換する.
- トライアゾール-ディアゾイミン均衡によるアザビニル金属カルベンの形成.
- ヘテロサイクルのコア変換の実証.
結論:
- 新しいRh(II) 誘導法により,さまざまなイミダゾロンとチアゾールにアクセスできます.
- 反応は,提案されたアザビニル金属カルベンの中間体を通過します.
- この方法論は,複雑なヘテロサイクルのスキャファードを構築するための貴重なツールを提供します.
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