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Synthesis 1989; 1989(2): 139-141
DOI: 10.1055/s-1989-27178
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A Facile Synthesis of 2-Methyl-4-oxo-4,5-dihydrofuro [3,2-c]quinolines

V. Sudhakar Rao* , Malleshwar Darbarwar
  • *Department of Chemistry, Osmania University, Hyderabad 500007, India
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Publication Date:
17 September 2002 (online)

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A facile route to 2-methyl-4-oxo-4,5-dihydrofuro[3,2-c]quinolines 5a-d has been developed by base-catalyzed thermal rearrangement of 4-(2-propynyl)oxyquinolin-2(1H)-ones 4a-d in good yields. The propynylation of 4-hydroxyquinolin-2(1H)-ones 1a-d furnished 3,3-di(2-propynyl)-2,4-dioxo-1,2,3,4-tetrahydroquinolines 2a-d, 4-(2-propynyl)oxy-3-(2-propynyl)quinolin-2(1H)-ones 3a-d, and 4a-d. A mechanistic pathway for the formation of 5 from 4 via 6 and 7 has been described.