Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 13, Pages 4312-4316Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202005124
Keywords
azaoxyallyl cations; benzoxazepinediones; copper; cyclization; hypervalent iodine reagents
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Funding
- National Natural Science Foundation of China [21672172]
- project of Youth Science and Technology Innovation Team of Sichuan Province, China [2017TD0008]
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In this study, a [3+2] cycloaddition reaction of aza-oxyallylic cations with ethynylbenziodoxolones was developed for the synthesis of new lambda(3)-iodanes containing spirocyclic 4-oxazolidinone. These cyclic lambda(3)-iodanes exhibit stability in air and excellent solubility in organic solvents, and can be used as substrates for the high-yield synthesis of 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives under copper(I)-catalyzed conditions.
Herein, a [3+2] cycloaddition of aza-oxyallylic cations with ethynylbenziodoxolones for synthesis of new lambda(3)-iodanes containing spirocyclic 4-oxazolidinone has been developed. This cyclic lambda(3)-iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives were afforded in high yield under copper(I)-catalyzed conditions.
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