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

Yan Luo; Chun-Hua Chen; Jin-Qi Zhang; Cui Liang; Dong-Liang Mo

doi:10.1055/s-0039-1691490

Synthesis, Table of Contents

Synthesis 2020; 52(03): 424-432
DOI: 10.1055/s-0039-1691490

paper

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

Yan Luo

,

Chun-Hua Chen

,

Jin-Qi Zhang

,

Cui Liang

,

Dong-Liang Mo ∗

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China Email: moeastlight@mailbox.gxnu.edu.cn

› Author Affiliations

Abstract

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^‡ Yan Luo and Chun-Hua Chen contributed equally to this work.

Abstract

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.

Key words

9-fluorenone nitrones - [3+3] cycloaddition - aza-oxyallyl cations - metal-free - spiroheterocycles

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References

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Supplementary Material

Supporting Information