26177-05-9Relevant articles and documents
Reaction of Methyl N-Oxido-quinolyl and -isoquinolyl Ketone Oximes with Tosyl Chloride
Tagawa, Yoshinobu,Honjo, Noriko,Goto, Yoshinobu
, p. 564 - 571 (2007/10/02)
The reactions of (E)-methyl 1-oxido-2-quinolyl ketone oxime (VE), (E)- and (Z)-methyl 1-oxido-4-quinolyl ketone oxime (VIIE and VIIZ) and (Z)-methyl 2-oxido-1-isoquinolyl ketone oxime (IXZ) with tosyl chloride in the presence of NaOH were investigated to compare the reactivity of the N-oxide with that of the oxime group in the same molecule.In the reaction of VE, 1-hydroxy-2-(1H)-quinolinone (XII) and 2(1H)-quinolinone (XIII) were obtained by the elimination of the acetoxime group.The mechanism of the formation of XII and XIII is discussed in detail.In the reaction of VIIE, Beckmann rearrangement occurred to afford 4-acetylaminoquinoline 1-oxide (XVIII), while the reactions of VIIZ and IXZ gave only the tosylates of the oximes.These results demonstrate that there is a large difference of reactivity between the E-form and the Z-form, and further that VE and VIIE show markedly differnt chemical behavior.Keywords - methyl 1-oxido-quinolyl ketone oxime; methyl 2-oxido-1-isoquinolyl ketone oxime; E-form; Z-form; steric compression effect; 13C-NMR; acetoxime group elimination; tosylation; Beckmann rearrangement
