21083-13-6Relevant academic research and scientific papers
1-diarylmethyl-1,2-diozetidin-3-one derivatives
-
, (2008/06/13)
There are disclosed compounds having the formula STR1 wherein R1 is hydrogen, alkyl of 1-10 carbon atoms, phenyl or phenyl substituted with halo, lower alkyl, lower alkoxy, nitro, cyano or lower alkoxycarbonyl; R2 and R3 are phenyl or phenyl mono- or di- substituted with halo, lower alkyl, lower alkoxy, nitro, cyano, diloweralkylamino or lower alkoxycarbonyl and R2 and R3 may be the same or different; and R4 is alkyl of 1-10 carbon atoms, phenyl or phenyl mono- or di- substituted with halo, lower alkyl, lower alkoxy, cyano, nitro or lower alkoxycarbonyl; and their use as antifungal agents.
Synthesis and properties of 3-oxo-1,2-diazetidinium ylides
Taylor, Edward C.,Haley, Neil F.,Clemens, Robert J.
, p. 7743 - 7752 (2007/12/18)
Treatment of α-chloroacylhydrazones of diaryl and certain aralkyl and dialkyl ketones with sodium hydride in anhydrous tetrahydrofuran gives 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium inner salts (ylides). The reaction pathway involves formation of the hydrazone anion followed by intramolecular SN2 halide displacement (with complete inversion at the α carbon) by the sp2 imine nitrogen. These 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium ylides are reduced by sodium borohydride to give 1-substituted 1,2-diazetidin-3-ones, undergo dipolar cycloaddition reactions to give fused aza-β-lactams, and can be hydrolyzed with p-toluenesulfonic acid monohydrate to the p-toluenesulfonic acid salt of 1,2-diazetidinone.
