Synthesis of Spirofluorenyl-1,2,4-oxadiazinan-5-ones through Metal-Free [3+3] Cycloaddition of N -Vinyl Fluorenone Nitrones with Aza-oxyallyl Cations.

Spirofluorenyl-1,2,4-oxadiazinan-5-ones are prepared in good to excellent yields through metal-free [3+3] cycloaddition of N -vinyl fluorenone nitrones and aza-oxyallyl cations under mild reaction conditions. Detailed studies reveal that N -vinyl fluorenone nitrones show greater reactivity in [3+3] cycloadditions with aza-oxyallyl cations compared to N -alkyl/aryl fluorenone nitrones. The spirofluorenyl-1,2,4-oxadiazinan-5-ones are easily prepared on gram scale. The present method features mild reaction conditions, broad substrate scope, good functional group tolerance and efficient [3+3] cycloadditions of 9-fluorenone nitrones. [ABSTRACT FROM AUTHOR]