An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones

  • Yadav P
  • Ahmad G
  • Maurya R
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Abstract

An efficient route for the syntheses of β-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3-(benzothiophene-5-yl)- 1,3-diketones in very good yields. © 2005 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Isoxazoles
  • Isoxazolines
  • Oxime-olefin cycloaddition
  • Pongamol
  • β-Hydroxychalcones

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Authors

  • Prem P. Yadav

  • Ghufran Ahmad

  • Rakesh Maurya

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