The reaction of 1-alkyl-3,4-dinitropyrroles with secondary amines gives nucleophilic aromatic cine substitution (formation of 1-alkyl-2-amino-4-nitropyrroles), whereas the reaction with primary amines follows a more complicated pattern, involving mainly a multistep ring-opening and ring-closure process, and also yielding the product of formal direct substitution, but not that of cine substitution.
P. Mencarelli and F. Stegel, J. Chem. Soc., Chem. Commun., 1980, 123 DOI: 10.1039/C39800000123
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