98815-40-8Relevant articles and documents
Stereoselective and catalytic access to β-enaminones: An entry to pyrimidines
Gayon, Eric,Szymczyk, Monika,Vrancken, Emmanuel,Campagne, Jean-Marc,Gerard, Helene
, p. 9205 - 9220,16 (2012/12/11)
We describe herein a highly stereoselective access to Cbz-protected β-enaminones 2 based on the NaOH catalyzed rearrangement of propargylic hydroxylamines 1. The synthetic potential of these β-enaminones is illustrated in an original synthesis of pyrimidi
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.