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Divergent synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2023 Dec 20; Vol. 22 (1), pp. 90-94. Date of Electronic Publication: 2023 Dec 20. - Publication Year :
- 2023
-
Abstract
- Indole-3-carbinol, bisindolylmethanes (BIMs) and indole-3-methanamines exhibit diverse therapeutic activities. Fluorinated molecules are widely used in pharmaceuticals. Herein we report a facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines by a Friedel-Crafts reaction. The reaction involves the in situ generation of difluoroacetaldehyde from difluoroacetaldehyde ethyl hemiacetal in the presence of a base or an acid. This protocol is distinguished by its good to excellent yields, broad substrate compatibility, good functional group tolerance and scalability.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 22
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 38047717
- Full Text :
- https://doi.org/10.1039/d3ob01735d