[3 + 3] Formal Cycloadditions of Nitrones from Isatins and Azaoxyallyl Cations for Construction of Spirooxindoles. Issue 6 (31st March 2017)

• Record Type: Journal Article
• Authors: Lin, Weijia; Zhan, Gu; Shi, Minglin; Du, Wei; Chen, Yingchun
• Is Part Of: Chinese journal of chemistry. Volume 35:Issue 6(2017)
• Page Start: 857
• Page End: 860
• Publication Date: 2017-03-31
• Subjects: cycloaddition -- spirooxindoles -- azaoxyallyl cations -- nitrones -- 1, 3‐dipoles; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201600864
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract : A [3 + 3] formal cycloaddition reaction between in situ formed azaoxyallyl cations and nitrones from isatins has been developed, furnishing a spectrum of spiro[1, 2, 4‐oxadiazinan‐5‐one]oxindoles in good to excellent yields with excellent diastereoselectivity. This method provides direct and efficient access to potentially bioactive spirooxindoles incorporating a six‐membered heterocyclic scaffold. Abstract : Spirooxindoles incorporating a six‐membered heterocyclic scaffold are efficiently constructed through a [3 + 3] formal cycloaddition reaction between nitrones from isatins and α ‐halohydroxamates under basic conditions.