1. Matthias Brewer, The University of Vermont, Burlington Vermont, 05405
Concise and efficient routes to nitrogen heterocycles by way of a novel ring fragmentation reaction
Matthias Brewer, The University of Vermont, Burlington Vermont, 05405
Ring fragmentation reactions hold a special position in organic synthesis because they can provide compounds that are otherwise difficult to prepare and they can result in big structural changes in the molecule that are not possible to achieve by other means. Unfortunately, very few synthetically useful fragmentation reactions are known. With the generous financial support provided by the ACS- PRF we have developed the novel ring fragmentation reaction shown below. This fragmentation is quite general and provides useful synthetic intermediates.
We have also discovered that the products formed by this fragmentation are convenient precursors to polycyclic nitrogen-containing heterocycles. While there is a long history of research devoted to developing methods for the synthesis of nitrogen-containing heterocycles, structurally complex polycyclic heterocycles are still challenging to prepare. Our research is providing an efficient and concise method to prepare these important compounds.