3-Azido-2-methoxyindolines as safe and stable precursors to overcome the instability of fleeting 3-azidoindoles

Use of 3-azidoindoles in organic synthesis remains a difficult task owing to their instabilities. Herein, we report a general and concise approach for tackling this problem by using 3-azidoindole surrogates. The surrogates are bench-stable, presumably due to the observed intramolecular O-N β bonding...

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Published in:Chemical communications (Cambridge, England) England), 2021-12, Vol.57 (98), p.13381-13384
Main Authors: Yamashiro, Toshiki, Abe, Takumi, Tanioka, Masaru, Kamino, Shinichiro, Sawada, Daisuke
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Summary:Use of 3-azidoindoles in organic synthesis remains a difficult task owing to their instabilities. Herein, we report a general and concise approach for tackling this problem by using 3-azidoindole surrogates. The surrogates are bench-stable, presumably due to the observed intramolecular O-N β bonding. The resultant fleeting intermediates undergo capturing in situ to afford 3-substitued indoles through formal ipso -substitution of the azide group by nucleophiles. In these investigations, we found that the fleeting 3-azidoindoles show a C3-electrophilic character for the first time. We have developed 3-azido-2-methoxyindolines (AZINs) as user-friendly, bench-stable, thermally stable and reactive 3-azidoindole surrogates for the first time.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06033c