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

Jie Li, Wen Wen Zhang, Xiao Jing Wei, Feng Liu, Wen Juan Hao, Shu Liang Wang, Guigen Li, Shu Jiang Tu, Bo Jiang

Research output: Contribution to journalArticle

23 Scopus citations

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.

Original languageEnglish
Pages (from-to)6621-6628
Number of pages8
JournalJournal of Organic Chemistry
Volume82
Issue number13
DOIs
StatePublished - Jul 7 2017

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