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DOI: 10.1055/s-2007-966019
Antimycobacterial Benzofuro[3,2-f]chromenes from a 5-Bromochromen-6-ol
Publication History
Publication Date:
18 April 2007 (online)
Abstract
In the course of our work on the synthesis of analogues of the specific antimycobacterial 3,3-dimethyl-3H-benzofuro[3,2-f]chromene, we prepared the previously unreported 5-bromo-2,2-dimethyl-2H-chromen-6-ol. We wish to report here an original synthetic scheme using this compound. The preparation of various 5-bromo-2,2-dimethyl-6-(aryloxy)-2H-chromenes was first investigated. This was followed by a palladium-catalysed cyclisation reaction, which takes place only in the presence of air, and leads to 3,3-dimethyl-3H-benzofuro[3,2-f]chromenes or 3,3-dimethyl-3H-4,7-dioxa-10-aza-benzo[c]fluorene. The antimycobacterial properties of these analogues have been investigated.
Key words
nucleophilic aromatic substitutions - cyclisations - medicinal chemistry - catalysis - palladium
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References
Current address: Laboratoire de Chimie et Biochimie des Substances Naturelles, UMR 5154 CNRS/MNHN-USM 0502 MNHN, Muséum National d’Histoire Naturelle, 57 rue Cuvier CP54, 75005 Paris, France.