Synthesis and physico-chemical properties of some l-benzyl-azepane-2,3-dione 3-(O-substituted oximes) with attribution of their Ζ and Ε configurations and 4-(phenylhydrazono)azepane-2,3-dione 3-(0-substituted oximes) resulting of condensation with various O-aryl-hydroxylamines are described. These azepanedione-oxime compounds are prepared from the corresponding azepan-2-ones and 1-benzylazepan-2-ones.
IntroductionThrough studies of amide or lactame derivatives highlighted the interesting pharmacological properties, in particular actions on central nervous system via stimulation of various ion channels [1], The synthesis of 3-[0-(benzyl)oximinoether] hexahydroazepin-2,3-diones previously reported [2] showed that they are capable to relax both rat trachea and human bronchus. The oximinoether or oxime derivatives exhibited marked antinociceptive and anticonvulsant activities [3], This work describes synthesis and physicochemical properties of l-benzylazepane-2,3-dione 3-(0-substituted oximes) with attribution of their Ζ and Ε configurations and 4-(phenylhydrazono)azepane-2,3-dione 3-(0-substituted oximes) resulting of condensation with various O-arylhydroxylamines from the corresponding azepan-2-ones and 1 -benzylazepan-2-ones.
CI3HlaN2OsS, Mr = 310.315, monoclinic, P2t, a = 5.607 (5), b = 13.296 (5), c = 9.833 (8) A, /~ = 90.67 (5) °, V = 733 (1) A 3, Z = 2, Ox = 1.406 Mg m -3, A(Mo K~) = 0-7107/~, /z = 0-245 mm-t, F(000) = 324, T = 295 K, final R = 0.045 for 1280 unique observed reflections. In the solid state the C6Ha--NO2 group is s-trans with respect to the ethyl ester: this structure corresponds to the major component in solution. The N(2)--C(7) bond length shows that N--CO has a double-bond character. The thiazolidine ring may be considered as of the envelope type.Introduction. ~H and ~3C NMR spectra (Hamri, 1985) of amides of 4-thiazolidinecarboxylic acid ethyl ester, unsubstituted on C2, realized at different temperatures, indicate the existence, in solution, of two different and inseparable conformations.
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