Radical Deaminative ipso-Cyclization of 4-Methoxyanilines with 1,7-Enynes for Accessing Spirocyclohexadienone-Containing Cyclopenta[c]quinolin-4-ones
Radical Deaminative ipso-Cyclization of 4-Methoxyanilines with 1,7-Enynes for Accessing Spirocyclohexadienone-Containing Cyclopenta[c]quinolin-4-ones
复制标题
4-甲氧基苯胺与 1,7-烯炔的自由基脱氨基原环化以获得含有螺环己二烯酮的环戊[c]喹啉-4-酮
DOI：
10.1021/acs.joc.7b00704
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发表时间：
2017
影响因子：
3.6
通讯作者：
Jiang Bo
中科院分区：
文献类型：
--
作者：
Li Jie;Zhang Wen-Wen;Wei Xiao-Jing;Liu Feng;Hao Wen-Juan;Wang Shu-Liang;Li Guigen;Tu Shu-Jiang;Jiang Bo
在温和的条件下，建立了一个新的由C-中心自由基引发的N-栓系1，7-烯炔类化合物的环化级联反应，用于与两个全碳的四元立体中心形成28个具有生物意义的螺环己二烯酮[c]喹啉-4-酮。由4-甲氧基苯胺和t-Buono原位生成的重氮盐作为4-甲氧基苯基的前体，无需添加氧化剂，使6-exo-digcyclization/5-exo-trigipso-cyclization能够通过无金属脱芳构化构建三个新的C-C键。该反应还具有底物范围广、环化效率高、官能团耐受性高等特点。
A new C-center radical-triggered bicyclization cascade ofN-tethered 1,7-enynes for forming 28 examples of biologically interesting spirocyclohexadienone-containing cyclopenta[c]quinolin-4-ones with two all-carbon quaternary stereocenters has been established under mild conditions. The in situ generated diazonium salts from 4-methoxyanilines andt-BuONO are served as 4-methoxyphenyl precursors without additional oxidant, enabling 6-exo-digcyclization/5-exo-trigipso-cyclization to construct three new C–C bonds through metal-free dearomatization. The reaction also features broad substrate scope, annulation efficiency, and high functional group tolerance.