REACTIONS OF ALIPHATIC NITRO-COMPOUNDS AND GLYCOCYAMIDINES

Acylation reaction of aliphatic nitro compounds (1) with acetyl chloride in the presence of glycocyamidine (2a) afforded 4-(1,2,4-oxadiazol-5-yl)methyl-1,2,4-oxadiazol-5(4H)-one (4) and their imino derivatives (5). The reaction was applied to creatinine (2b) and 1,3-dialkylglycocyamidine (2d-2h) to give N-methyl-N-(1,2,4-oxadiazol-5-yl)[(1,2,4-oxadiazol-5-yl)methylamine] (6) and 5-substituted 1,2,4-oxadiazole derivatives (9, 11), respectively. The mechanism of formation of these products appears to involve 1,3-dipolar cycloaddition of nitrile oxides with imine intermediates (A, B, C, or D) which result from N-3-C-2 cleavage of imidazolidine ring of 2.