Synthesis 1993; 1993(6): 623-626
DOI: 10.1055/s-1993-25914
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A Novel Rearrangement of 3-Arylisoxazol-5(4H)-ones: One-Pot Synthesis of New 2,4-Dichloroquinoline-3-carbaldehydes

K. Ashok* , G. Sridevi, Y. Umadevi
  • *Department of Chemistry, Nizam College, Osmania University, Hyderabad 500 001, India
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17. September 2002 (online)

Vilsmeier-Haack reaction, using a specific combination of phosphorus oxychloride and dimethylformamide, on 3-arylisoxazol-5(4H)-ones 1 resulted in 2,4-dichloroquinoline-3-carbaldehydes 6 as the major products along with other minor products, through a novel rearrangement. Oxidation of 6 with alkaline potassium permanganate gave 2,4-dichloroquinoline-3-carboxylic acids 7. Decarbonylation of 6 and decarboxylation of 7 using aqueous sodium hydroxide yielded 2,4-dichloroquinolines 8. All the compounds were characterised by elemental and spectral analysis.