On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone DerivativesThis 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).
Received: 19 April 2017
Accepted after revision: 14 June 2017
25 July 2017 (eFirst)
◊ These authors contributed equally to this work
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.