Azole- and δ2-azolinecarbaldehyde oximes and their derivatives

The production of 1-methyl-substituted pyrazole-, imidazole-, ²-pyrazoline-, and ²-imidazolinecarbaldehyde oximes is described. The alkylation of 1-methylimidazole-and 1-methyl-²-pyrazolinecarbaldehyde oximes with methyl iodide and ,-dihalo-genoalkanes forms quaternary and bisquaternary ammonium derivatives, respectively. The quaternary derivatives of 1-methylpyrazolecarbaldehyde oximes are obtained by the oximation of the corresponding quaternary derivatives of the aldehydes; the direct methylation of these oximes either does not take place or leads to the formation of nitrones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1093–1098, August, 1973.The melting points were determined on a Kofler block.