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Paper | Regular issue | Vol 45, No. 8, 1997, pp.1467-1475
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7735
Studies in Sigmatropic Rearrangement of 3-(4-Aryloxybut-2-ynyloxy)-1-methylquinolin-2-ones: Synthesis of 3H-Pyrano[2,3-c]quinolin-5(6H)-ones and Furo[2,3-c]quinolin-4(5H)-ones

Krishna C. Majumdar* and Anup K. Kundu

*Department of Chemistry, University of Kalyani, Kalyani-741 325, W. B., India


3-(4-Aryloxybut-2-ynyloxy)-1-methylquinolin-2-ones (3), in refluxing chlorobenzene, gave 1-aryloxymethyl-6-methyl-3H-pyrano[2,3-c]quinolin-5(6H)-ones (4) and/or, 1-aryloxymethyl-2,5-dimethylfuro[2,3-c]quinolin-4(5H)-ones (5). The base or the radical initiator (azoisobutyronitirle) does not seem to have any effect on the formation of the products. Substrates (3) provided only products (5) in the presence of toluene-4-sulphonic acid. All the substrates (3) studied so far underwent sigmatropic rearrangements at the 4-quinolin-3-ynyoloxypropynyl function of compound (3) to give products (4) and/or (5).