1187168-46-2Relevant academic research and scientific papers
An efficient 3-acylquinoline synthesis from acetophenones and anthranil: Via C(sp3)-H bond activation mediated by Selectfluor
Gao, Yejun,Hider, Robert C.,Ma, Yongmin
, p. 10340 - 10344 (2019/04/10)
An efficient method for the synthesis of 3-functionalized quinolines from commercially available acetophenones and anthranil has been described. Selectfluor propels the C(sp3)-H bond activation of the acetophenones and aza-Michael addition of anthranil resulting in annulated 3-acylquinolines in moderate to high yields. DMSO acts not only as a solvent but also as a one carbon donor in the reaction.
One-pot phosphine-catalyzed syntheses of quinolines
Khong, San,Kwon, Ohyun
, p. 8257 - 8267,11 (2020/10/15)
In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4- disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the β-phosphonium enoate α-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile Ntosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.
