Functionalized heterocycles are emerging as fundamental components of organic chemistry, and synthesis pathways for these molecules are increasingly gaining attention from chemists and pharmaceutical companies.  This research involves Hemetsberger-Knittel nitrene insertion reaction coupled with decarboxylation of the azidocinnamate to yield the subsequent azido acid.  This acid is exposed to microreactor technology, instigating thermal cyclization and producing substituted indole products.  We are optimizing synthesis of substituted indoles by investigating time and temperature variations during microwave-assisted synthesis as well as solvent environments for the azido acid cyclization, and use of copper chromite catalyst during the reaction.  These factors are tested on 2, 3, and 4-substituted azido acids and effectiveness of the reaction conditions is quantified based on product purity versus presence of starting material or formation of intermediates.  One-pot nitrene insertion- decarboxylation is being explored in attempt to eliminate issues with product decomposition during thermolysis and low product purity after reaction completion.

Microwave-assisted one-pot nitrene insertion-decarboxylation synthesis of substituted indoles

243rd National Meeting (2012)

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