1-Phenyl-4-imidazolidinone (Z)-Oxime

Oximes as Intermediates or Final Products in Reactions of Nitroheteroarenes with Nucleophiles in the Presence of Sodium Methoxide‐Methanol System.

“…Results of 11 X-ray analysis are shown below ( Figure 6 and Tables 6 -7). The formation of O-methyl derivative of the expected oxime 13 from nitropyrazole 3 ( Table 5, Scheme 3), under the conditions used here, seems to confirm some slightly different behavior between the nitrosoimidazoles and nitrosopyrazoles, observed also in the hydride reduction [5]. As we have already mentioned, the hydride reduction of 4-nitroimidazoles affords oximes of imidazolones or imidazolidinones.…”

“…A similar reduction of 4-nitropyrazole gives 4,4'-azoxypyrazole. In both reactions, respective nitroso derivatives have been postulated as intermediates [5]. Probably the nitroso group, in the pyrazole derivatives, is more susceptible to nucleophiles than that of the imidazoles.…”

“…TLC plates (Merck, silica gel 60F 254 ) were developed in UV and in iodide vapors. 2-Nitrothiophene (4), 1-nitronaphthalene (5) and solvents were commercially purchased. Starting 4-nitroimidazoles 1, 2, 7 were obtained according to the procedure published earlier by us [2].…”

“…25 °C for 48 hours; therefore, the conditions were close to those that we used earlier [1 -4]. For a comparison, we also looked for product structures of similar reactions of phenylacetonitrile carbanion with 4-nitro-1-phenylpyrazole (3), 2-nitrothiophene (4), and 1nitronaphthalene (5). In the case of the latter three starting nitrocompounds, further transformations of oximes would be much less likely than in the case of nitroimidazoles.…”