Highly Efficient Synthesis of CF3-Containing 7-Aminoquinolines From Cyclocondensation Reaction of Trifluoroacetyl Enamine Precursors

Highly Efficient Synthesis of CF3-Containing 7-Aminoquinolines From Cyclocondensation Reaction of Trifluoroacetyl Enamine Precursors

Andrighetto, Rosália; Bonacorso, Helio G.; Navarini, Jussara; Krüger, Nícolas; Martins, Marcos A. P.; Zanatta, Nilo

Abstract:

The quinoline ring system occurs in numerous natural products, especially in alkaloids, and presents a wide spectrum of physiological activities. Much attention is still being given to the synthesis of quinoline derivatives because of their industrial applications and pharmacological properties. Trifluoromethyl substituted quinolines are the subject of growing interest because of their medicinal importance, particularly as antimalarial agents (e.g., mefloquine and halofantrine). Since the classical antimalarial molecules are encountering increased drug resistance, considerable efforts have been directed toward the synthesis of new fluorinated quinolines that can provide improved anti-parasitic activity. The purpose of this work is to report the results of a chemical behavior study of the reactions of ketones 1 with 2,6-diaminotoluene (2,6-DAT).

The quinoline ring system occurs in numerous natural products, especially in alkaloids, and presents a wide spectrum of physiological activities. Much attention is still being given to the synthesis of quinoline derivatives because of their industrial applications and pharmacological properties. Trifluoromethyl substituted quinolines are the subject of growing interest because of their medicinal importance, particularly as antimalarial agents (e.g., mefloquine and halofantrine). Since the classical antimalarial molecules are encountering increased drug resistance, considerable efforts have been directed toward the synthesis of new fluorinated quinolines that can provide improved anti-parasitic activity. The purpose of this work is to report the results of a chemical behavior study of the reactions of ketones 1 with 2,6-diaminotoluene (2,6-DAT).

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DOI: 10.5151/chempro-14bmos-R0008-1

Referências bibliográficas

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• [5] 5 a) Bonacorso, H. G.; Duarte, S. H. G.; Zanatta, N.; Martins, M. A. P. Synthesis 2002, 1037. b) Bonacorso, H. G.; Andrighetto, R.; Zanatta, N.; Martins, M. A. P. Tetrahedron Lett. 2010, 51, 3752.

Como citar:

Andrighetto, Rosália; Bonacorso, Helio G.; Navarini, Jussara; Krüger, Nícolas; Martins, Marcos A. P.; Zanatta, Nilo; "Highly Efficient Synthesis of CF3-Containing 7-Aminoquinolines From Cyclocondensation Reaction of Trifluoroacetyl Enamine Precursors", p-8-8. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0008-1