The goal of this research is to develop a new synthetic method for generating 3-hydroxychromones substituted at the 2 position with aryl groups. Flavonols are commonly made by condensation reactions, which have several limitations. The new synthetic approach involves the Suzuki coupling reaction of 2-bromo-3-benzyloxychromone with aryl boronic acids to afford 2-aryl-3-benzyloxychromone. The resulting compounds are then deprotected to give 2-aryl-3-hydroxychromone. The success of this method will be reported as will the structures of intermediates 3-bromo-3-hydroxychromone and 3-benzyloxy-2-phenylchromone. Using both established procedures and the new synthetic method, some novel 2-aryl-3-hydroxychromones have been prepared. Examples of ortho- and para-substituted phenyl groups and fluorescent groups have been attached at the 2 position of the hydroxychromone. The results of structural and photophysical studies will be reported. These will be interpreted in terms of the electronic communication (or lack thereof) of the 2-aryl group with the chromone portion of the molecule.

Synthetic studies towards 2-aryl-3-hydroxychromones (flavonols): Structures and spectroscopic characterization of products

245th National Meeting (2013)

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