Brønsted Acid-Catalyzed Straightforward Synthesis of Benzo[b]carbazoles from 2,3-Unsubstituted Indoles

Described is a general and efficient synthesis of valuable benzo[b]carbazoles by Brønsted acid‐catalyzed reactions between simple C‐2,C‐3‐unsubstituted indoles and ortho‐[α‐(hydroxy)benzyl]benzaldehyde acetals. Highly selective migration processes are involved as key steps in the overall cascade seq...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2014-02, Vol.356 (2-3), p.374-382
Main Authors: Suárez, Anisley, García-García, Patricia, Fernández-Rodríguez, Manuel A., Sanz, Roberto
Format: Article
Language:English
Subjects:
1,2‐alkyl shift
2-alkyl shift
benzo[b]carbazoles
Brønsted acid catalysis
heterocycles
synthetic methods
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Summary:Described is a general and efficient synthesis of valuable benzo[b]carbazoles by Brønsted acid‐catalyzed reactions between simple C‐2,C‐3‐unsubstituted indoles and ortho‐[α‐(hydroxy)benzyl]benzaldehyde acetals. Highly selective migration processes are involved as key steps in the overall cascade sequence that involves the one‐pot formation of two new bonds and a cycle in a regioselective fashion.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201300868