Facile approach to multifunctionalized 5-alkylidene-3-pyrrolin-2-ones via regioselective oxidative cyclization of 2, 4-pentanediones with primary amines and sodium sulfinates. Issue 15 (27th June 2022)

• Record Type: Journal Article
• Authors: Liu, Donghan; Lu, Xihang; Zhang, Qiaohe; Zhao, Yuxuan; Zhang, Biao; Sun, Yulin; Dai, Weifeng; Xu, Yu; Yu, Fuchao
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 15(2022)
• Page Start: 4078
• Page End: 4084
• Publication Date: 2022-06-27
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00473a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Highly functionalized 5-alkylidene-3-pyrrolin-2-ones were efficiently synthesized via a four-component cascade cyclization/sulfonylation reaction between readily available 2, 4-pentanediones, primary amines and sodium sulfinates under mild conditions. Abstract : A multi-component cascade cyclization reaction of readily available 2, 4-pentanediones, primary amines and sodium sulfinates is reported. Highly functionalized 5-alkylidene-3-pyrrolin-2-ones were efficiently synthesized in moderate to excellent yields under mild conditions. This cascade cyclization was achieved by direct regioselective transformation of C(sp 3 )–H bonds at two weakly nucleophilic sites in the enaminone intermediate while two strongly nucleophilic sites of the structure were not involved.