Catalyst-free synthesis of quinoline-enols through coupling between heterocyclic N-oxides and CF3-ynones under mild conditions. Issue 22 (29th September 2022)

• Record Type: Journal Article
• Authors: Chang, Zhenbang; Zhang, Saisai; Wang, Yinpeng; Xiong, Heng-Ying; Zhang, Guangwu
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 22(2022)
• Page Start: 6200
• Page End: 6204
• Publication Date: 2022-09-29
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01260j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The coupling between heterocyclic N -oxides and CF3 -ynones has been demonstrated via the formal C–H and C–C bond cleavage under catalyst-free and mild conditions. Abstract : The coupling between heterocyclic N -oxides and CF3 -ynones has been demonstrated via the formal C–H and C–C bond cleavage under catalyst-free and mild conditions. This reaction displays a broad substrate scope of CF3 -ynone and heterocyclic N -oxide coupling partners (>60 examples). The gram scale synthesis and smooth transformation of the coupling adduct indicate the potential application of this approach. Preliminary mechanistic studies suggest that [3 + 2] annulation and the retro-Claisen reaction are the key steps for the formation of quinoline-enol scaffolds.