Additive-free synthesis of fused tricyclic cyanoisoxazolidines using in situ formed cyanonitrones. Issue 4 (15th December 2022)

• Record Type: Journal Article
• Authors: Jamali, Muhammad Fahad; Yadav, Usha; Babu, Mary Merlin Manjaly; Kant, Ruchir; Mohanan, Kishor
• Is Part Of: Chemical communications. Volume 59:Issue 4(2023)
• Page Start: 446
• Page End: 449
• Publication Date: 2022-12-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc05831f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : 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. Abstract : 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.