Synthesis of cyano-substituted γ-lactams through a copper-catalyzed cascade cyclization/cyanation reaction. Issue 6 (17th January 2023)

• Record Type: Journal Article
• Authors: Liu, Wen; Wang, Liang; Mu, Haiping; Zhang, Qian; Fang, Zeguo; Li, Dong
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 6(2023)
• Page Start: 1168
• Page End: 1171
• Publication Date: 2023-01-17
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob02086f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A copper-catalyzed cascade cyclization/cyanation of N -aryl-4-pentenamides with TMSCN was developed. The reaction proceeded in water under simple conditions to generate a series of cyano-substituted γ-lactam derivatives. Abstract : A convenient copper-catalyzed cascade cyclization/cyanation reaction for the construction of cyano-containing γ-lactams was developed. The protocol employed TMSCN as the cyano source and proceeded in water under simple conditions. Mechanistic studies indicated this reaction involved an amidyl radical initiated cascade 5- exo-trig cyclization/cyanation process. It is capable of generating a series of cyano-substituted γ-lactams and relative 2-oxazolidinone derivatives with a broad substrate scope.