Convenient One-Pot Synthesis of N-Substituted 3-Trifluoroacetyl Pyrroles

Zanatta, Nilo; Wouters, Ana Dionéia; Fantinel, Leonardo; Silva, Fábio de Moraes Vaz da; Barichello, Rosemário; Silva, Pedro Eduardo Almeida da; Soares, Daniela Fernandes Ramos; Bonacorso, Helio Gauze; Martins, Marcos Antonio Pinto


A new one-pot strategy for the synthesis of a series of new N-substituted 3-trifluoroacetyl pyrroles is presented. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5- dihydrofuran with primary amines, which generated 1,1,1-trifluoro- 3-(2-hydroxyethyl)-4-alkylaminobut-3-en-2-one intermediates. In most cases these intermediates were not stable enough to be isolated. Thus, in the same reaction vessel they were directly submitted to oxidation with PCC (Corey’s reagent) to furnish 1,1,1-trifluoro- 3-(2-ethanal)-4-alkylaminobut-3-en-2-ones, which under reflux underwent intramolecular cyclization to give the desired N-substituted 3-trifluoroacetyl pyrroles, in moderate yields. All of these pyrroles were tested against pan-susceptible Mycobacterium tuberculosis H37Rv and clinical isolates INH- and RMP-resistant strain and some of these compounds showed significant in vitro antimicrobial activity.

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