3
References and notes
A
mechanistic proposal for multicomponent reaction
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promoted by NbCl5 is showed in Scheme 2. Probably, a
Knoevenagel condensation reaction between the aldehyde
derivative and methyl acetoacetate initially occurs, forming the
benzylidene derivative in situ. The β-ketoester becomes prone to
attack due to keto-enol tautomerism and the attack takes place on
the carbon of the aldehyde, which is more electrophilic due to the
complexation with the niobium pentachloride. The benzylidene
derivative reacts with the second equivalent of methyl acetate
through Michael addition reaction, followed by a closing ring
reaction to obtain the 4H-pyran derivative.
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Scheme 2. Mechanistic proposal for multicomponent reaction
promoted by NbCl5.
Finally, we can conclude that the use of niobium
pentachloride as a catalyst in the multicomponent reaction
between methyl acetoacetate (1) and benzaldehyde derivatives (2
a-g) produces new 4H-pyran derivatives with good yields, under
mild reaction conditions (room temperature) in a very efficient
manner.
Acknowledgments
The authors would like to thank Fundação de Amparo à
Pesquisa do Estado de São Paulo (FAPESP) (Proc. 2016/01599-
1), Conselho Nacional de Desenvolvimento Científico
e
8.
(a) Arpini, B. H.; Bartolomeu, A. A.; Andrade, C. K. Z.; da Silva-
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Chem. 2015, 52, 273; (c) Bartolomeu, A. A.; Menezes, M. L.; da
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Tecnológico (CNPq) (Proc. 302753/2015-0) and Pró-Reitoria de
Pesquisa (PROPe-UNESP) for their financial support. We would
also like to thank CBMM – Companhia Brasileira de Mineralogia
e Mineração for the NbCl5 samples.
Supplementary data
Supplementary data associated with this article can be found
in the online version.