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Evidence is presented for the involvement of ketene intermediates in the thermal transformations of ethyl 4-nitro-1H-imidazol-5-ylethanoates into 4H-imidazo(4,5-c)isoxazole derivatives. Direct heterocyclisation of a 1-(4-nitro-1H-imidazol-5-yl)-3-phenylcarbodiimide intermediate is proposed to account for the reaction of a triphenyl N-(4-nitro-1H-imidazol-5-yl)phosphinimine with phenyl isocyanate exemplifying a new, flexible, and potentially general route to 2-aryl- 2H,4H-imidazo(4,5-d)(1,2,3)triazoles.

Aspects of heterocyclisation reactions mediated by nucleophilic interaction of aromatic nitro groups with ortho heterocumulene side chains