Unprecedented ring cleavage in the reaction of 1-methyl-3-phenacyl benzimidazolium ylide with diethyl azodicarboxylate

The reaction with diethyl azodicarboxylate (DEAZD) of different cycloimmonium ylides derived from pyridinium, quinolinium, isoquinolinium and 1-methylbenzimidazolium bromides (3, 4, 5 and 6) yielded 3-substituted tetraazapentenes (2). In the special case of 1-methyl-3-phenacyl-benzimidazolium bromide (6a), the ring cleavage compound N-[1-[(ethoxycarbonyl)amino]-2-oxo-2-phenylethylidene]-N-formyl-N-methyl-1,2-benzenediamine (7a) was obtained. Its structure was established by X-ray crystallography.