Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/Propargylation-Cyclization

被引：61
作者：
Fan, Jinmin
Wan, Changfeng
Sun, Gaojun
Wang, Zhiyong [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Joint Lab Green Synthet Chem, Hefei 230026, Anhui, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 21期
关键词：
D O I：
10.1021/jo8017654
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.
引用
收藏
页码：8608 / 8611
页数：4
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