Stereoselective hydrogenation of 3-acyl-substituted 2- (trifluoromethyl)-2H-chromen-5-one and chromane scaffolds in NaBH4 /ethanol medium

Stereoselective hydrogenation of 3-acyl-substituted 2- (trifluoromethyl)-2H-chromen-5-one and chromane scaffolds in NaBH4 /ethanol medium

Navarini, Jussara; (PQ), Helio G. Bonacorso; Wiethan, Carson W.; Pittaluga, Everton P.; Junges, Andrizia F.; Luz, Fábio M.; Martins, Marcos A. P.; Zanatta, Nilo

Abstract:

Octahydrochromens are compounds that contain a non-aromatic cyclic ether nucleus of tetrahydropyran, which are part of a wide array of natural compounds, as well as synthetic flavors substances. For this reason, there is a clear growth in the employing of some of them as flavor and perfume compounds in certain odorants. On the other hand, the reducing agent sodium borohydride is commonly used for reduction of unsaturated carbonyl compounds, is becoming a standard method in both academic and industrial laboratories. In this context, we describe a synthesis of a new series of substituted octahydrochromenone derivatives (2) from the 2-trifluoromethyl-2Hchromenones (1) and one example of 3,4-dihydro- 2H-chromane (4) from the respective 2- (trifluoromethyl)chromane (3), employing sodium borohydride/ethanol as an efficient, straightforward and selective reductive reaction medium for these types of heterocyclic compounds.

Octahydrochromens are compounds that contain a non-aromatic cyclic ether nucleus of tetrahydropyran, which are part of a wide array of natural compounds, as well as synthetic flavors substances. For this reason, there is a clear growth in the employing of some of them as flavor and perfume compounds in certain odorants. On the other hand, the reducing agent sodium borohydride is commonly used for reduction of unsaturated carbonyl compounds, is becoming a standard method in both academic and industrial laboratories. In this context, we describe a synthesis of a new series of substituted octahydrochromenone derivatives (2) from the 2-trifluoromethyl-2Hchromenones (1) and one example of 3,4-dihydro- 2H-chromane (4) from the respective 2- (trifluoromethyl)chromane (3), employing sodium borohydride/ethanol as an efficient, straightforward and selective reductive reaction medium for these types of heterocyclic compounds.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013104165710

Referências bibliográficas

• [1] 1 Macedo, A.; Wendler, E.P.; Santos, A.A.; Zuckerman-Schpector, J.; Tieking, E.R.T. J. Braz. Chem. Soc. 2010, 21, 1563.
• [2] 2 (a) Hudlicky, M. Reduction in Organic Chemistry, Ellis Horwood Ltd, Chichester, 1984. (b) Augustine, R. L. Heterogeneous Catalysis for the Synthetic Chemist, Marcel Dekker: New York, 1995.
• [3] 3 Bonacorso, H. G.; Navarini, J.; Wiethan, C. W.; Bortolotto, G. P.; Paim, G.R.; Cavinatto, S.; Martins, M.A.; Zanatta, N.; Caro, M. S. B. J. Fluorine Chem. 2011, 132, 166.
• [4] 4 Bonacorso, H.G.; Navarini, J.; Wiethan, C.W.; Junges, A.F.; Cavinatto, S.; Andrighetto, R.; Martins, M.A.P.; Zanatta, N. J. Fluorine Chem. 2012, 142, 90.

Como citar:

Navarini, Jussara; (PQ), Helio G. Bonacorso; Wiethan, Carson W.; Pittaluga, Everton P.; Junges, Andrizia F.; Luz, Fábio M.; Martins, Marcos A. P.; Zanatta, Nilo; "Stereoselective hydrogenation of 3-acyl-substituted 2- (trifluoromethyl)-2H-chromen-5-one and chromane scaffolds in NaBH4 /ethanol medium", p-138-138. 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_2013104165710