Selective oxidative aromatization of polyfunctionalized trifluoromethyl substituted chromenones by microwave irradiation

Selective oxidative aromatization of polyfunctionalized trifluoromethyl substituted chromenones by microwave irradiation

Cavinatto, Susiane; Navarini, Jussara; Wiethan, Carson W.; Junges, Andrizia F.; Pittaluga, Everton P.; Luz, Fábio M.; Paim, Gisele R.; Martins, Marcos A. P.; Zanatta, Nilo; Bonacorso., Helio G.

Abstract:

The synthesis of fluoroorganic compounds is a challenging topic of the modern organic chemistry. Specially, the presence of trifluoromethyl moiety in the target molecule often results in significant changes of its physical, chemical and biological properties. In addition, chromenones are not only important biologically active compounds and natural products but also valuable substrates for the synthesis of related pharmacologically interesting compounds. In this context, we decided to study the oxidative aromatization of a series of trifluoromethylsubstituted chromenones, which we had been previously synthesized in our laboratory. Considering the importance of the heterocyclic precursors 1 and product 2 the aim of this work is to report the synthesis of series of high substituted chromane derivatives from the 2-trifluoromethyl-2Hchromenones (1) employing iodine/alcohol as an efficient and selective oxidative medium with microwave (MW) irradiation procedure.

The synthesis of fluoroorganic compounds is a challenging topic of the modern organic chemistry. Specially, the presence of trifluoromethyl moiety in the target molecule often results in significant changes of its physical, chemical and biological properties. In addition, chromenones are not only important biologically active compounds and natural products but also valuable substrates for the synthesis of related pharmacologically interesting compounds. In this context, we decided to study the oxidative aromatization of a series of trifluoromethylsubstituted chromenones, which we had been previously synthesized in our laboratory. Considering the importance of the heterocyclic precursors 1 and product 2 the aim of this work is to report the synthesis of series of high substituted chromane derivatives from the 2-trifluoromethyl-2Hchromenones (1) employing iodine/alcohol as an efficient and selective oxidative medium with microwave (MW) irradiation procedure.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201361017598

Referências bibliográficas

• [1] 1(a) Chambers, R. D. Fluorine Org. Chem. Blackwell, Oxford, 2004; (b) Kirsh, P. Modern Fluoroorganic Chem., Wiley-VCH, Weinheim, Germany, 2004; (c) Begue, J. P.; Bonnet-Delpon, D. Bioorg. Med. Chem. Fluorine, Wiley, Hoboken, NJ, 2008; (d) Maienfish, P.; Hall, R. G. Chimia 2004, 58, 93; (e) Liu, Z. P. Current Org. Chem. 2010, 14, 888; (f) Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 1, 104.
• [2] 2 Bonacorso, H.G.; Navarini, J.; Wiethan, C.W.; Bortolotto, G.P.; Paim, G.R.; Cavinatto, S.; Martins, M. A. P.; Zanatta, N.; Caro, M.S.B. J. Fluorine Chem. 2010, 132, 160.
• [3] 3 Mphahlele, J. M.; Moekwa, B. T. Org. Biomol. Chem. 2005, 3, 2469.
• [4] 4 Rueping, M.; Sugiono, E. E. Merino, Chem. Eur. J. 2008, 14, 632.
• [5] 5Bonacorso, G. H.; Navarini, J.; Wiethan, C. W.; Andrighetto, R.; Junges, A. F.; Cavinatto, S.; Martins, M. A. P.; Zanatta, N. J. Fluorine Chem. 2012,142, 90.

Como citar:

Cavinatto, Susiane; Navarini, Jussara; Wiethan, Carson W.; Junges, Andrizia F.; Pittaluga, Everton P.; Luz, Fábio M.; Paim, Gisele R.; Martins, Marcos A. P.; Zanatta, Nilo; Bonacorso., Helio G.; "Selective oxidative aromatization of polyfunctionalized trifluoromethyl substituted chromenones by microwave irradiation", p-33-33. 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_201361017598