Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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
Shu-Jiang Tu, Guigen Li, Bo Jiang, Feng Liu, Xiao-Jing Wei, Shu-Liang Wang, Wen-Juan Hao, Jie Li, Wen-Wen Zhang
A new C-center radical-triggered bicyclization cascade of N-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 and t-BuONO are served as 4-methoxyphenyl precursors without additional oxidant, enabling 6-exo-dig cyclization/5-exo-trig ipso-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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00704

DOI: 10.1021/acs.joc.7b00704

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