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.
Fan
Jinmin
J
Joint laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, PR China.
Wan
Changfeng
C
Sun
Gaojun
G
Wang
Zhiyong
Z
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