13243-54-4Relevant academic research and scientific papers
Synthesis of Isomeric Series of Aryltetrahydrobenzisoxazoles and Arylcyclopentisoxazoles
Fos, Empar,Borras, Liset,Gasull, Maria,Mauleon, David,Carganico Germano
, p. 203 - 208 (2007/10/02)
Four series of potential PAF-antagonists in which the isoxazole nucleus is condensed with a polyhydrogenated five- or six-carbon ring were prepared.The synthesis of the compounds 3-aryl-4,5,6,7-tetrahydrobenzisoxazoles 1, 3-arylcyclopentisoxazole 2,
Metal-carbonyl-Induced Reaction of Isoxazoles. Ring Cleavage and Reduction by Hexacarbonylmolybdenum, Pentacarbonyliron, or Nonacarbonyldi-iron
Nitta, Makoto,Kobayashi, Tomoshige
, p. 1401 - 1406 (2007/10/02)
In the presence of and water the isoxazoles (1a-f) undergo thermally induced reductive cleavage of the N-O bond to give β-amino enones in good yield.Similar results were obtained by the use of and water with photoirradiation, or of and water with heating.A mechanism involving an N-complexed isoxazolepentacarbonylmolybdenum or isoxazoletetracarbonyliron, and a - or -complexed (β-oxo vinyl)nitrene intermediate is proposed for the reactions.The complexed nitrene moiety could be reduced by the central metal in the presence of water to give amine.Furthermore, treatment of 2-benzoyl- 3-phenyl-2-H-azirine (8a), which is an isomer of 3,5-diphenylisoxazole, with the metal carbonyls and water also resulted in the formation of a β-amino enone possibly via the corresponding complexed (β-oxo vinyl)nitrene.An N-complexed isoxazole-pentacarbonylmolybdenum intermediate was prepared by the photoreaction of with 3,5-dimethylisoxazole.Its characterization, and chemical transformations, have been carried out to investigate the proposed mechanism.
