Para‐TsOH‐Promoted Cascade Reaction of ortho‐Propynol Phenyl Azides for the Synthesis of 4‐Methoxy Quinolines and Propargyl Methyl Ethers: Insight on Mechanism of Propargylic Alcohols. Issue 3 (12th February 2019)

• Record Type: Journal Article
• Authors: Yang, Tao; Ding, Haixin; Li, Ren; Jin, Fengyan; Song, Xian‐Rong; Chen, Xi; Bai, Jiang; Xiao, Qiang; Liang, Yong‐Min
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 3(2019)
• Page Start: 391
• Page End: 398
• Publication Date: 2019-02-12
• Subjects: propargylic alcohols -- azides -- cascade reaction -- 4-methoxy quinolines -- propargyl methyl ethers; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900047
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: para ‐TsOH‐promoted cascade reaction of easily prepared ortho ‐propynol phenyl azides for the synthesis of 4‐methoxy quinolines has been developed. This reaction proceeded in a new way to generate 4‐methoxy quinolines through a concerted nucleophilic mechanism of propargyl methyl ether. It is worth noting that propargyl methyl ether can be successfully transformed into 4‐methoxy quinolines only when substrates contain a strong electron‐donating group (OR). Abstract : Let's cycle to quinoline ! para ‐TsOH‐promoted cascade reaction of easily prepared ortho ‐propynol phenyl azides for the synthesis of 4‐methoxy quinolines has been developed. This reaction proceeded in a new way to generate 4‐methoxy quinolines through a concerted nucleophilic mechanism of propargyl methyl ether. It is worth noting that propargyl methyl ether can be successfully transformed into 4‐methoxy quinolines only when substrates contain a strong electron‐donating group.