1,2-Diazine N-oxides are bench-top stable starting materials rendering them useful building blocks for complex molecules. The photochemistry of 1,2-diazine N-oxides has not been rigorously exploited in synthesis because of the lack of regioselective oxidation of non-symmetric pyridazines. However, they possess the potential for development of many reaction processes such as ring-opening and photoreduction. We recently developed the photochemical ring-opening of functionalized pyridazine N-oxides. Furthermore, we studied the photochemical ring-opening of functionalized pyridazine N-oxides to synthesize pyrazoles. We have extended this photochemistry through the photolysis of pyridazine N-oxides with subsequent insertion by rhodium-metal catalysts providing valuable secondary reactions. Consequently, it allows for entry to heterocyclic scaffolds found within certain natural products such as carbazoles and dibenzofurans.

Photochemistry of pyridazine N-oxides: A versatile tool for heterocycle synthesis

2019 Spring National Meeting

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