Synthesis, Characterization of Spirocyclic λ3‐Iodanes and Their Application to Prepare 4,1‐Benzoxazepine‐2,5‐diones and 1,3‐Diynes

Herein, a [3+2] cycloaddition of aza‐oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3‐iodanes containing spirocyclic 4‐oxazolidinone has been developed. This cyclic λ3‐iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both th...

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Bibliographic Details
Published in:Chemistry : a European journal 2021-03, Vol.27 (13), p.4312-4316
Main Authors: Sun, Xu, Guo, Xiao‐Qiang, Chen, Lian‐Mei, Kang, Tai‐Ran
Format: Article
Language:English
Subjects:
azaoxyallyl cations
benzoxazepinediones
Cations
Chemistry
copper
cyclization
Cycloaddition
hypervalent iodine reagents
Substrates
Synthesis
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Summary:Herein, a [3+2] cycloaddition of aza‐oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3‐iodanes containing spirocyclic 4‐oxazolidinone has been developed. This cyclic λ3‐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. The spirocyclic hypervalent iodine reagents containing 4‐oxazolidinone ring are prepared via a (3+2)‐cycloaddition of azaoxyallyl cations with ethynylbenziodoxolones. They display satisfactory stability and solubility in organic solvents. Using them as precursors, both 4,1‐benzoxazepine‐2,5‐diones and 1,3‐diynes derivatives were afforded in one‐pot under copper (I)‐catalyzed conditions.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202005124