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Original Synthesis of Substituted 6H-Benzo[c]chromene Derivatives Using a TDAE and Pd-Catalyzed Cyclization Strategy
Donia Ben Salah1,2, Omar Khoumeri3, Theo-Bob Muller3
1Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif 2050, Tunisia.
Abstract:
We report an efficient synthetic method for the preparation of 6H-benzo[c]chromenes from substituted 1-(2'-bromo-[1,1'-biphenyl]-2-yl)-2-phenylethanols. These intermediates were obtained via a TDAE-initiated reaction between new substituted 2'-bromo-[1,1'-biphenyl]-2-carbaldehyde derivatives and substituted nitrobenzylic chlorides. The second step involved a palladium-catalyzed intramolecular O-arylation of the alcohol intermediate under microwave irradiation (110 °C for 1.5 h). The structure of 6H-benzo[c]chromene derivatives was confirmed by X-ray crystallography of product 5c.
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