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Synthesis 2017; 49(21): 4845-4852
DOI: 10.1055/s-0036-1589072
DOI: 10.1055/s-0036-1589072
paper
On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives
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).Weitere Informationen
Publikationsverlauf
Received: 19. April 2017
Accepted after revision: 14. Juni 2017
Publikationsdatum:
25. Juli 2017 (online)
◊ 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
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589072.
- Supporting Information
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