Department of Chemistry, Indian Institute of Technology Madras , Chennai, Tamil Nadu 600036, India.
Org Lett. 2015 Feb 6;17(3):406-9. doi: 10.1021/ol503683q. Epub 2015 Jan 29.
A metal-free one-pot strategy has been developed for the first time to synthesize pharmaceutically important α-amino ketones from readily available benzylic secondary alcohols and amines using N-bromosuccinimide. This new reaction proceeds via three consecutive steps involving oxidation of alcohols, α-bromination of ketones, and nucleophilic substitution of α-bromo ketones to give α-amino ketones. Importantly, this novel one-pot greener reaction avoids direct usage of toxic and corrosive bromine. This methodology has been employed efficiently to synthesize pharmaceutically important amfepramone and pyrovalerone in a single step.
首次开发了一种无金属的一锅法策略,可使用 N-溴代丁二酰亚胺(N-bromosuccinimide)从易得的苄基仲醇和胺合成具有重要药用价值的α-氨基酮。此新反应通过三个连续步骤进行,包括醇的氧化、酮的α-溴化以及α-溴代酮的亲核取代,从而生成α-氨基酮。重要的是,这种新颖的绿色一锅法反应避免了有毒和腐蚀性溴的直接使用。该方法已成功用于一步法合成具有重要药用价值的苯甲曲秦和吡咯戊酮。