2015年10月2日
Synthesis of Azepines via a [6 + 1] Annulation of Ynenitriles with Reformatsky Reagents.
The Journal of organic chemistry
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- 巻
- 80
- 号
- 19
- 開始ページ
- 9480
- 終了ページ
- 94
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/acs.joc.5b01397
A protocol for the direct synthesis of azepines using a hafnium(III)-catalyzed [6 + 1] annulation of N-tethered ynenitriles with Reformatsky reagents is reported. A broad range of 3-amino-2,7-dihydro-1H-azepine-4-carboxylates 4aa-4he were obtained in high yields and with excellent functional group tolerance. The copper-mediated reactions of isolable Blaise intermediates (enamino esters 3), uniquely underwent 5-endo cyclization to afford the β-2,5-dihydropyrrolyl α,β-unsaturated esters 5aa-5fc, which exhibit anticancer activity.
- ID情報
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- DOI : 10.1021/acs.joc.5b01397
- ISSN : 1520-6904
- PubMed ID : 26348544