Setembro 2013 vol. 1 num. 1 - Brazilian Meeting on Organic Synthesis 2011

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Chemoselective fluorination of 2-hydroxy-3,4,7,8-tetrahydro- 2H-chromen-5(6H)-ones using DAST

Porte, Liliane M. F. ; Bonacorso, Helio G. ; Paim, Gisele R. ; Navarini, Jussara ; Zanatta, Nilo ; Martins., Marcos A. P. ;

Abstract:

Multi-component reactions (MCRs), by virtue of their convergence, productivity, facile execution, and generally high yields of products, have attracted much attention from the vantage point of combinatorial chemistry. On the other hand, fluorine substitution can alter the chemical properties, disposition, and biological activity of drugs. Fluorine substitution can also have a profound effect on drug disposition, in terms of distribution, drug clearance, route(s), and extent of drug metabolism. Such changes can be used constructively by medicinal chemists to improve both the safety and the efficacy of a drug. Thus, considering the importance described and with base in works previously published by us, the aim of this work is to report a facile, efficient and chemoselective fluorination of 2-hydroxy-2Hchromenones 1 using DAST (diethylaminosulfur trifluoride).

Abstract:

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Palavras-chave: DAST, chromenones, fluorination,

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DOI: 10.5151/chempro-14bmos-R0147-1

Referências bibliográficas
  • [1] 1 Rueping, M.; Sugiono, E.; Merino, E. Chem. Eur. J. 2008, 14, 6329.
  • [2] 2 Dollery, C. Therapeutic Drugs. Edinburgh, Churchill Livingstone, UK, 1999.
  • [3] 3 (a) 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. 2011, 132, 160.(b) Bonacorso, H. G.; Porte, L .M. F.; Paim,
  • [4] G. R.; Luz, F. M.; Martins, M. A. P.; Zanatta, N. Tetrahedron Lett. 2010, 51, 3759.
Como citar:

Porte, Liliane M. F.; Bonacorso, Helio G.; Paim, Gisele R.; Navarini, Jussara; Zanatta, Nilo; Martins., Marcos A. P.; "Chemoselective fluorination of 2-hydroxy-3,4,7,8-tetrahydro- 2H-chromen-5(6H)-ones using DAST", p. 147 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-14bmos-R0147-1

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