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Paper | Regular issue | Vol 32, No. 10, 1991, pp.1973-1981
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5829
Rearrangement of N-Ureidopyrroles: A Case of Mononuclear Heterocyclic Rearrangement Involving an Aromatic Heterocycle as Carbon-Nitrogen-Nitrogen Sequence

Gabriella Macaluso, Giuseppe Cusmano,* Girolamo Cirrincione, Anna Maria Almerico, and Patrizia Diana

*Dipartimento di Chimica Organica, Università digli Studi di Palermo, Via Archirafi 20 90123 Palermo, Italy

Abstract

The rearrangement, under basic conditions, of the N-ureidopyrroles (8) directly led to the pyrrolylalkenes (14). The reaction was explained in terms of initial mononuclear heterocyclic rearrangement leading to the pyrrolo[1,2-c][1,2,3]triazoles (12) followed by their decomposition to the final products under the reaction conditions. Attempts to thermally rearrange compound (8b) only gave products of decomposition of the ureido moiety.