Additive-free synthesis of fused tricyclic cyanoisoxazolidines using formed cyanonitrones

Herein, we disclose the first report on the generation of cyanonitrone in situ from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access fused tricyclic cyanoisoxazolidines. Further, this methodology could be extended to access fused tricyclic...

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Published inChemical communications (Cambridge, England) Vol. 59; no. 4; pp. 446 - 449
Main Authors Jamali, Muhammad Fahad, Yadav, Usha, Babu, Mary Merlin Manjaly, Kant, Ruchir, Mohanan, Kishor
Format Journal Article
Published 05.01.2023
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Summary:Herein, we disclose the first report on the generation of cyanonitrone in situ from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access fused tricyclic cyanoisoxazolidines. Further, this methodology could be extended to access fused tricyclic trifluoromethylated and phosphonylated isoxazolidines. Surprisingly, the reductive ring-opening of cyanoisoxazolidines was followed by a spontaneous lactonization to produce fused tricyclic amino lactones. Moreover, the N-O bond of the obtained tricyclic trifluoromethylated isoxazolidines could be cleaved to obtain 1,3-amino alcohols. Herein, we disclose the generation of cyanonitrone from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access an important class of fused tricyclic cyanoisoxazolidines.
Bibliography:For ESI and crystallographic data in CIF or other electronic format see DOI
https://doi.org/10.1039/d2cc05831f
Electronic supplementary information (ESI) available: Detailed experimental procedures, complete characterization data, CIF for
copies of NMR spectra. CCDC
2091413
5a
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc05831f