New strategy for the synthesis of 4-amine-2-trifluoromethyl pyrroles N-substituted

New strategy for the synthesis of 4-amine-2-trifluoromethyl pyrroles N-substituted

Aquino, Estefania da C.; Zanatta, Nilo; Gariboti, Vanessa C.; Bonacorso, Helio G.; Martins, Marcos A. P.

Abstract:

Pyrroles are one the most important class of heterocyclic compounds that are frequently found in many natural products and bioactive molecules. Furthermore, trifluoromethyl substituted pyrroles are rare compounds; however, they have been show to exhibit significant insecticidal and acaricidal activity. The introduction of fluorine atoms and fluorinated groups into organic molecules often confers significant and useful changes in their chemical and physical properties. Fluorinated enaminones are also very attractive synthons with high potential for the synthesis of fluorinated heterocycles. In this work, we present a versatile approach for the synthesis of a new series of 4-amine-3- trifluoromethyl pyrroles N-substituted from β- enaminones trifluoromethylate 2 with amines.

Pyrroles are one the most important class of heterocyclic compounds that are frequently found in many natural products and bioactive molecules. Furthermore, trifluoromethyl substituted pyrroles are rare compounds; however, they have been show to exhibit significant insecticidal and acaricidal activity. The introduction of fluorine atoms and fluorinated groups into organic molecules often confers significant and useful changes in their chemical and physical properties. Fluorinated enaminones are also very attractive synthons with high potential for the synthesis of fluorinated heterocycles. In this work, we present a versatile approach for the synthesis of a new series of 4-amine-3- trifluoromethyl pyrroles N-substituted from β- enaminones trifluoromethylate 2 with amines.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201383205848

Referências bibliográficas

• [1] 1 Zanatta, N.; Aquino, E. da C.; Silva, F. M. da; Bonacorso, H. G.; Martins, M. A. P. Synthesis 2012, 44, 3477.
• [2] 2 Zanatta, N.; Schneider, J. M. F. M.; Schneider, P. H.; Wouters, A. D.; Bonacorso, H. G.; Martins, M. A. P.; Wessjohann, L. A. J. Org. Chem. 2006, 71, 6996.
• [3] 3 Martins, M. A. P.; Sinhorim, A. P.; Frizzo, C. P.; Buriol, L.; Scapin, E.; Zanatta, N.; Bonacorso, H. G. J. Heterocyclic Chem. 2013, 50, 71.
• [4] 4 Lyutenko, N. V.; Gerus, I. I.; Kacharov, A. D.; Kukhar, V. P. Tetrahedron 2003, 59, 1731.

Como citar:

Aquino, Estefania da C.; Zanatta, Nilo; Gariboti, Vanessa C.; Bonacorso, Helio G.; Martins, Marcos A. P.; "New strategy for the synthesis of 4-amine-2-trifluoromethyl pyrroles N-substituted", p-63-63. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201383205848