Synthesis of indolizines, pyrrolones and indolizinones

Simple heterocycles are the work-horse of modern medicinal chemistry, but unfortunately they don’t get as much attention, at least in academia, as more sterochemically complex molecules. I have had many instances where I needed to make a certain heterocyclic target but found that there was very little, if any, literature precedent concerning the heterocycle I was interested in. It is refreshing to find academic types developing new methods for the synthesis of heterocylic systems.

An interesting paper in Org. Lett. from the Sarpong group at UC Berkeley involves a simple method for the synthesis of pyridine fused heterocycles starting from readily available starting materials. The key step in the method involves a Pt(II) catalyzed ring closure which subsequently undergoes proton transfer and/or rearrangement to provide 5 or 8, depending on the subtituent attached to the carbinol center.

pyridine3.gif

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