Palladium-catalyzed dearomatizative [2 + 2 + 1] carboannulation of 1,7-enynes with aryl diazonium salts and H2O: facile synthesis of spirocyclohexadienone-fused cyclopenta[c]quinolin-4(5H)-ones

Yu Liu; Ren-Jie Song; Jin-Heng Li

doi:10.1039/C7CC02830J

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Palladium-catalyzed dearomatizative [2 + 2 + 1] carboannulation of 1,7-enynes with aryl diazonium salts and H₂O: facile synthesis of spirocyclohexadienone-fused cyclopenta[c]quinolin-4(5H)-ones†

Yu Liu,^ab Ren-Jie Song*^a and Jin-Heng Li

*^ab

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* Corresponding authors

^a Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
E-mail: jhli@hnu.edu.cn, srj0731@hnu.edu.cn

^b State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China

Abstract

A new palladium-catalyzed dearomatizative [2 + 2 + 1] carboannulation of 1,7-enynes with aryl diazonium salts and H₂O is presented. The reaction enables the construction of spirocyclohexadienone-fused cyclopenta[c]quinolin-4(5H)-ones through a sequence of Heck-type addition, 6-exo-dig cyclization, ipso-cyclization, dearomatization and hydrolysis.

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Article information

DOI: https://doi.org/10.1039/C7CC02830J
Article type: Communication
Submitted: 12 Apr 2017
Accepted: 07 Jul 2017
First published: 07 Jul 2017

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Chem. Commun., 2017,53, 8600-8603

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Palladium-catalyzed dearomatizative [2 + 2 + 1] carboannulation of 1,7-enynes with aryl diazonium salts and H₂O: facile synthesis of spirocyclohexadienone-fused cyclopenta[c]quinolin-4(5H)-ones

Y. Liu, R. Song and J. Li, Chem. Commun., 2017, 53, 8600 DOI: 10.1039/C7CC02830J

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Chemical Communications