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

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The use of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD) in multicomponent reactions. Synthesis of acetoacetanilides, pyridones and dihydropyrimidines.

Gama, Fernando H. de Souza ; Garden, Simon J. ;

Abstract:

Multi-component reactions, where more than two reagents combine to give a product in a one-pot process, are efficient methods for the construction of otherwise complex skeletal structures. An important group of substrates for such reactions are 1,3- dicarbonyl compounds. One of the oldest multicomponent reactions known is the Biginelli reaction. This three component reaction involves the condensation of urea, ethyl acetoacetate and a benzaldehyde. Biginelli products, dihydropyrimidines, posses a wide variety of biological activities. In this study we investigated the reaction of TMD (1) with anilines (2) for the preparation of acetoacetanilides (3) in apolar (toluene and xylene) and polar protic (water) solvents. Additionally, the one pot four component reaction involving 1, 2, urea (4) and benzaldehydes (5) to give Biginelli products (6) was studied (Figure 1).

Abstract:

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Palavras-chave: acetylketene, aqueous reaction medium, condensation reactions,

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DOI: 10.5151/chempro-14bmos-R0273-1

Referências bibliográficas
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  • [3] 3 Souza, R.O.M.A.; Penha, E.T.; Milagre, H.M.S.; Garden, S.J.; Esteves, P.M.; Eberlin, M.N.; Antunes, O.A.C. Chem. Eur. J. 2009, 15, 9799.
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  • [5] 5 Huggins, M. T., Barber, P. S., Florian, D., Howton, W., Synth. Commun., 2008, 38, 4226; Clemens, R. J., Hyatt, J. A., J. Org. Chem., 1985, 50, 2431.
Como citar:

Gama, Fernando H. de Souza; Garden, Simon J.; "The use of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD) in multicomponent reactions. Synthesis of acetoacetanilides, pyridones and dihydropyrimidines.", p. 273 . 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-R0273-1

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