Synthesis 2017; 49(21): 4845-4852
DOI: 10.1055/s-0036-1589072
paper
© Georg Thieme Verlag Stuttgart · New York

On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives

Hongpeng Suna, Li Xiaoa, Wei Lia, b, Qiong Xie*a, b, Liming Shao*a, b
  • aSchool of Pharmacy, Fudan University, 826 Zhangheng Road, Zhangjiang Hi-tech Park, Pudong, Shanghai 201203, P. R. of China   Email: limingshao@fudan.edu.cn   Email: qxie@fudan.edu.cn
  • bShanghai Center for Drug Discovery & Development, 826 Zhangheng Road, Zhangjiang Hi-tech Park, Pudong, Shanghai 201203, P. R. of China
This work was financially supported by the National Basic Research Program of China (973 Program, 2015CB931804) and Science and Technology Commission of Shanghai Municipality (No. 15431900100).
Further Information

Publication History

Received: 19 April 2017

Accepted after revision: 14 June 2017

Publication Date:
25 July 2017 (eFirst)

These authors contributed equally to this work

Abstract

Silver-catalyzed on-water intramolecular cyclization of acetylenic free amines is reported, which affords 7-azaindoles in good to excellent yields. Neither strong base/acid catalysts nor N-substituted substrates are required to achieve this cycloisomerization. Hydrogen bonds between water medium and the substrates play an important role in improving chemical reactivity and regioselectivity. Furthermore, the on-water reaction is extendable to acetylenic amides for isoquinolone synthesis.

Supporting Information