Synthesis 2016; 48(20): 3551-3558
DOI: 10.1055/s-0035-1562430
paper
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of 1-Aryl- and 2-Aryl-Substituted Indazolones via Intramolecular C–N Coupling Promoted by KOt-Bu

Wei-juan Wang
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China   Email: yanming@mail.sysu.edu.cn   Email: zhangxj33@mail.sysu.edu.cn
,
Jia-hua Chen
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China   Email: yanming@mail.sysu.edu.cn   Email: zhangxj33@mail.sysu.edu.cn
,
Zi-cong Chen
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China   Email: yanming@mail.sysu.edu.cn   Email: zhangxj33@mail.sysu.edu.cn
,
Yu-feng Zeng
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China   Email: yanming@mail.sysu.edu.cn   Email: zhangxj33@mail.sysu.edu.cn
,
Xue-jing Zhang*
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China   Email: yanming@mail.sysu.edu.cn   Email: zhangxj33@mail.sysu.edu.cn
,
Ming Yan*
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China   Email: yanming@mail.sysu.edu.cn   Email: zhangxj33@mail.sysu.edu.cn
,
Albert S. C. Chan
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China   Email: yanming@mail.sysu.edu.cn   Email: zhangxj33@mail.sysu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 06 March 2016

Accepted after revision: 03 May 2016

Publication Date:
07 June 2016 (online)


Abstract

A new method for the synthesis of 1-arylindazolones and 2-arylindazolones from N′-aryl-2-halobenzohydrazides promoted by KOt-Bu was developed. The difference of 2-halogen substituent exerted a significant effect on the distribution of the products. Two distinct reaction pathways are proposed for the generation of 1-arylindazolones and 2-arylindazolones, respectively.

Supporting Information

 
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