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Paper | Regular issue | Vol 32, No. 1, 1991, pp.73-78
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5599
A Regioselective Synthesis of 2-Alkylfuro[3,2-c]quinolin-4(5H)-ones

Krishna C. Majumdar* and Prabir K. Choudhury

*Department of Chemistry, University of Kalyani, Kalyani 741 235, West Bengal, India

Abstract

The title compounds (2a-h) were obtained in moderate yields by simply refluxing 1-alkyl-4-hydroxyquinolin-2(1H)-ones (1a,b) with a number of acetylenic halides in n-butanol in the presence of anhydrous potassium carbonate. Compounds (2h,i) were also obtained from 4-[2’-chloroprop-2-enyloxy][1]quinolin-2(1H)-ones (11a,b) via [3,3] sigmatropic rearrangement and cyclisation of the intermediate chloroallylic enols (13a,b) with aqueous ethanolic potassium hydroxide.