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Photoassisted [4+2] Cycloaddition Followed by Modification

Complex molecular structures have been shown to have a higher probability of biological activity, which has important implications for drug discovery and development; therefore, establishing methodologies that readily allow access to these structures is advantageous. Photochemistry offers a powerful and efficient synthetic strategy that can be utilized to achieve these challenging structures. Not to mention, photochemistry offers the exciting prospect of being “green” chemistry since the only reagent used is light. This project aims to synthesize complex nitrogen and sulfur-containing heterocycles using a photoassisted methodology. Photoprecursors can be synthesized by combining simple structures that undergo photoenolization, allowing for [4+2] Diels Alder cycloaddition, and then followed with postphotochemical modification. Using this approach, a fully aromatized product was isolated and rearrangement was possible. When published, this method will allow chemists to rapidly access complex structures, which are valuable to synthetic chemistry.

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