Facile Synthesis of Trisubstituted Carbazoles by Acid‐Catalyzed Ring‐Opening Annulation of 2‐Amidodihydrofurans with Indoles | Zendy

Zhao Jingjing | Zendy; Li Pan | Zendy; Xia Chungu | Zendy; Li Fuwei | Zendy

Premium

Facile Synthesis of Trisubstituted Carbazoles by Acid‐Catalyzed Ring‐Opening Annulation of 2‐Amidodihydrofurans with Indoles

Author(s) -

Zhao Jingjing,

Li Pan,

Xia Chungu,

Li Fuwei

Publication year - 2015

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201503260

Subject(s) - annulation , regioselectivity , chemistry , chemoselectivity , ring (chemistry) , catalysis , trifluoromethanesulfonate , trimethylsilyl , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry

A mild and convenient synthesis of carbazoles by TfOTMS (trimethylsilyl trifluoromethanesulfonate)‐catalyzed ring‐opening annulation of 2‐amidodihydrofurans is presented with a high degree of chemoselectivity and regioselectivity. This procedure was also scaled up to a gram‐scale synthesis. The reaction could involve an iminonium intermediate through a series of CO, CN bond cleavages, CC bond formations, and a 1,2‐migration process.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research