Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization.
Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amount 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 beta-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3-quinolinecarboxylic esters. The mechanistic details of this benzylation/propargylation and cyclization cascade process are also discussed.
Joint laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, PR China.
Jinmin
J
Fan
Changfeng
C
Wan
Gaojun
G
Sun
Zhiyong
Z
Wang
D000480:Alkynes; D019905:Benzyl Alcohol; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D020005:Propanols; D011804:Quinolines / Q000737:chemistry*
D000480:Alkynes; D004952:Esters; D020005:Propanols; D011804:Quinolines; C028255:propargyl alcohol; D019905:Benzyl Alcohol