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An Approach to 1,3,4-Oxadiazolidines via N,N'-Diborylated Hydrazine
Rong Jiang1, Yinlin Shao2,3, Juanjuan Jiang1
1School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China.
None:
We report a novel simple metal-free synthetic strategy that enables efficient access to highly substituted 1,3,4-oxadiazolidines that have remained synthetically elusive through conventional approaches from N,N'-diborylated hydrazines and aldehydes. This method also facilitates a one-pot protocol, wherein N,N'-diborylated hydrazine is generated in situ from azobenzene, 4,4'-bipyridine, and bis(pinacolato)diboron, followed by its reaction with aldehydes. The resulting 1,3,4-oxadiazolidines exhibit potential anti-inflammatory properties. Mechanistic insights, supported by DFT calculations, suggest a concerted aldehyde nitroboration-condensation cascade pathway for this transformation.
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