Synlett 2013; 24(18): 2431-2436
DOI: 10.1055/s-0033-1339671
letter
© Georg Thieme Verlag Stuttgart · New York

Isoquinoline N-Oxide Synthesis under Pd-Catalysed C–H Activation/Annulation Processes

Bingyao Li
a  Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Fax: +86(22)27404031   Email: jhuang@tju.edu.cn
b  Synergetic Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, P. R. of China
,
Pingxuan Jiao
a  Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Fax: +86(22)27404031   Email: jhuang@tju.edu.cn
,
Hongban Zhong
a  Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Fax: +86(22)27404031   Email: jhuang@tju.edu.cn
,
Jianhui Huang*
a  Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China   Fax: +86(22)27404031   Email: jhuang@tju.edu.cn
b  Synergetic Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 02 July 2013

Accepted after revision: 03 August 2013

Publication Date:
28 August 2013 (online)


Abstract

An oxime directed C–H activation–annulation reaction for the selective synthesis of a range of isoquinoline N-oxides has been developed. Under palladium-catalyzed acid-assisted conditions, the reaction undergoes concerted metallation deprotonation followed by carbopalladation and transmetallation to give poly­substituted isoquinoline N-oxides in moderate to good yields.

Supporting Information

 
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