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Radical Deaminative ipso-Cyclization of 4-Methoxyanilines with 1,7-Enynes for Accessing Spirocyclohexadienone-Containing Cyclopenta[c]quinolin-4-ones

Authors :
Jie Li
Bo Jiang
Shu-Liang Wang
Wen-Juan Hao
Xiao-Jing Wei
Shu-Jiang Tu
Guigen Li
Feng Liu
Wen-Wen Zhang
Source :
The Journal of Organic Chemistry. 82:6621-6628
Publication Year :
2017
Publisher :
American Chemical Society (ACS), 2017.

Abstract

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.

Details

ISSN :
15206904 and 00223263
Volume :
82
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....d7837104d803796859af0709d94b58bb