Over the past decade, John Gupton has established vinylogous amides as very versatile reagents for the regioselective synthesis of unsymmetrical, polysubstituted pyrroles.  All the chemistry to this point has employed standard batch synthesis methods. In particular, the reaction chemistry employs clean, high yield reactions which are ideal for conversion to flow chemistry techniques. We report here our attempts at optimizing continuous flow chemistry conditions for each of the reactions involved as well as for telescoped multistep syntheses to give the final polysubstituted pyrrole or azaisoflavinoids from starting ketones or acids/esters. <br/>

Flow chemistry implementation of the “Gupton vinylogous amide chemistry” for high yield, regiospecific, synthesis of unsymmetrical polysubstituted pyrroles and azaisoflavinoids

256th National Meeting (2018)

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