无金属催化的 N-芳基炔酰胺的邻/间位环化反应：3-硒代喹啉-2-酮和氮杂螺[4.5]癸-5-烯酮的发散合成。
Metal-free switchable ortho/ipso-cyclization of N-aryl alkynamides: divergent synthesis of 3-selenyl quinolin-2-ones and azaspiro[4,5]trienones.
机构信息
Department of Chemistry, Indian Institute of Technology Madras, Chennai - 600036, India.
出版信息
Org Biomol Chem. 2019 Dec 28;17(48):10163-10166. doi: 10.1039/c9ob02177a. Epub 2019 Nov 28.
PMID:31777902
Abstract
A selenium radical triggered switchable ortho/ipso-cyclization cascade of N-aryl alkynamides has been devised under metal-free conditions to access 3-selenyl quinolin-2-ones and 3-selenospiro[4,5]trienones in high yields (up to 98%). The simple protocol is scalable and the mechanistic studies suggest that the radical cascade proceeds through a spirocyclic intermediate which is formed via an intramolecular ipso-cyclization route.
摘要
在无金属条件下设计了一个硒自由基引发的可切换的 N-芳基炔酰胺的邻/间位环化级联反应，以高产率（高达 98%）得到 3-硒基喹啉-2-酮和 3-硒螺[4,5]三烯酮。该简单的方案具有可扩展性，并且机理研究表明，自由基级联反应通过通过分子内间位环化途径形成的螺环中间体进行。
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