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DOI: 10.1055/s-0039-1691490
Synthesis of Spirofluorenyl-1,2,4-oxadiazinan-5-ones through Metal-Free [3+3] Cycloaddition of N-Vinyl Fluorenone Nitrones with Aza-oxyallyl Cations
Financial support from the National Natural Science Foundation of China (21602037), the Natural Science Foundation of Guangxi Province (2016GXNSFFA380005), the Ministry of Education (IRT_16R15), the ‘Overseas 100 Talents Program’ of Guangxi Higher Education, and the ‘One Thousand Young and Middle-Aged College and University Backbone Teachers Cultivation Program’ of Guangxi are greatly appreciated.Publication History
Received: 27 October 2019
Accepted after revision: 31 October 2019
Publication Date:
13 November 2019 (online)
‡ 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 - spiroheterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691490.
- Supporting Information
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