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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
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2019-02-12 , DOI: 10.1002/ajoc.201900047
Tao Yang 1 , Haixin Ding 1 , Ren Li 1 , Fengyan Jin 1 , Xian-Rong Song 1 , Xi Chen 1 , Jiang Bai 1 , Qiang Xiao 1 , Yong-Min Liang 2
Affiliation  

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).

中文翻译:

邻苯丙酚苯叠氮化物的对-TsOH促进的级联反应,用于合成4-甲氧基喹啉和炔丙基甲基醚:炔丙醇机理的见解

已开发出对-TsOH促进的易于制备的丙炔丙二醇叠氮化物的级联反应,用于合成4-甲氧基喹啉。该反应以一种新的方式进行,通过炔丙基甲基醚的协同亲核机理生成4-甲氧基喹啉。值得注意的是,只有在底物包含强供电子基团(OR)时,炔丙基甲基醚才能成功转化为4-甲氧基喹啉。
更新日期:2019-02-12
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