Synthesis of 4-oxo-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazole-3-carboxylic acid esters

Coskun N., Yilmaz B.

SYNTHETIC COMMUNICATIONS, vol.34, no.9, pp.1617-1623, 2004 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 9
  • Publication Date: 2004
  • Doi Number: 10.1081/scc-120030749
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1617-1623


3-Imidazoline 3-oxides react regioselectively with 3-phenylpropanoic acid alkyl esters to give the corresponding 2-phenyl-3a,4,5,6-tetrahydroimidazol 1,5-b]isoxazole-3-carboxylic acid alkyl esters. This adducts convert to imidazole and the corresponding. alkyl 3-oxo-3-phenylpropanoic acid esters when treated with alkoxides or heated under vacuum. Attempts to oxidise the carbon-carbon double bond using KMnO4-FeSO4 led to the formation of heretofore unknown 4-oxo-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles.