An Oxidative [3+2+1] Cyclization of Enaminones and N‐Alkenyl‐2‐pyrrolidinone: Access to Polysubstituted 4‐Alkylated 1, 4‐dihydropyridines. Issue 8 (4th April 2023)

• Record Type: Journal Article
• Authors: Chai, Zhangmengjie; Chen, Longkun; Liu, Zhuoyuan; Sun, Yulin; Liu, Donghan; Zhang, Mingshuai; Wang, Yongchao; Yu, Fuchao
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 8(2023)
• Page Start: 1217
• Page End: 1223
• Publication Date: 2023-04-04
• Subjects: 4-Alkylated 1, 4-dihydropyridines -- Enaminones -- N-Alkenyl-2-pyrrolidinone -- Oxidative [3+2+1] cyclization -- Terminal olefin; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202300088
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An oxidative [3+2+1] cyclization of enaminones and N ‐alkenyl‐2‐pyrrolidinone is described for the synthesis of 4‐alkylated 1, 4‐dihydropyridines (1, 4‐DHPs). By using terminal olefin as the C4 source of the 1, 4‐DHP skeleton, this synthetic strategy provides a series of 1, 4‐DHPs through a 1, 1‐difunctionalization/cyclization process. In this protocol, two C( sp 3 )−C( sp 2 ) bonds and a C( sp 2 )−N bond are simultaneously formed, the hydrogen source on the newly formed methyl group of the 1, 4‐DHP skeleton is confirmed and a possible mechanism is proposed. Abstract :