Previously, we have optimized a new one-pot procedure for the reductive alkylation of various 2-hydroxybenzaldehydes (salicylaldehydes) where intramolecular cyclization occurs following the condensation step and several novel 4H-Chromenes were formed.  In this research, we apply 2-hydroxyacetophenone with malononitrile and base followed by sodium borohydride and the intermediate and product steps of the reaction were optimized.  Additional 2-hydroxyarylketones, prepared from phenols via esterification and Fries rearrangement, have been employed with additional optimization required.  Current progress in our laboratory on this reaction and further reactions on the novel products will be discussed.  Several of the chromenes have been submitted to the Open Innovation Drug Discovery (OIDD) with Eli Lilly & Company and their previous Phenotype Drug Discovery program.

Reductive alkylation of 2-hydroxyarylketones with malononitrile and borohydride

243rd National Meeting (2012)

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