Synthesis of New seleno[2,3-b]quinoline-2-carboxylates

B. P. Nandeshwarappa* B. Nagaraja and H. M. Manjunatha Swamy

Department of PG Studies and Research in Chemistry, Davangere University, Shivagangotri, Tholahunase - 577 007, INDIA. Department of Chemistry, S. J. M. Arts, Science and Commerce College, Chitrdurga - 577 501, INDIA.


A new method for the synthesis of substituted condensed seleno[2,3-b]quinoline-2-carboxylates derivatives has been achieved. Very first, 2-chloro-3-formylquinolines 2a-d are synthesized from substituted acetanilides 1a-d. Thus obtained 3-formyl-2-chloro-quinolines 2a-d were converted into substituted 2-seleno-3-formylquinolines 3a-d. Seleno quinolines thus obtained on refluxing with chloroacetic acid gave 3-formylquinolin-2-yl)seleno acetic acids 4a-d. Thus obtained on refluxing with methanol, ethanol and isopropanol in presence of POCl3 gave uncyclised substituted [(3-formylquinolin-2-yl)seleno]acetates 5a-d in quantitative yield. The cyclisation was achieved on refluxing with methanol in DMF at room temperature forms 6a-b. The structures of all the newly synthesized compounds were elucidated on the basis of elemental analysis, IR, 1H NMR and mass spectral data.

Keywords :3-Formyl-2-mercaptoquinolines; 3-Formyl-2-chloroquinolines; Seleno[2,3-b] quinolines; 3-Formylquinolin-2-yl)seleno acetic acids; Methyl seleno[2,3-b]quinoline-2-carboxylates.