The Journal of organic chemistry

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

J Fan, C Wan, G Sun, Z Wang

Index: Fan, Jinmin; Wan, Changfeng; Sun, Gaojun; Wang, Zhiyong Journal of Organic Chemistry, 2008 , vol. 73, # 21 p. 8608 - 8611

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Citation Number: 54

Abstract

Reactions of 2-amino-aryl alcohols with β-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 propargyl alcohols with β-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3-quinolinecarboxylic esters. The mechanistic details of this ...