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Química Nova

Print version ISSN 0100-4042On-line version ISSN 1678-7064

Abstract

GODOI, Marla N. et al. Síntese do monastrol e novos compostos de Biginelli promovida por In(OTf)3. Quím. Nova [online]. 2005, vol.28, n.6, pp.1010-1013. ISSN 0100-4042.  http://dx.doi.org/10.1590/S0100-40422005000600015.

In this paper, we describe a practical route for the synthesis of Biginelli compounds using In(OTf)3. To study the generality of this catalyst, several examples using aromatic aldehydes, 1,3-dicarbonyl compounds, urea, and thiourea were investigated. The present procedure provides an efficient modification of the classical Biginelli reaction, namely short reaction times and simple work-up, that not only preserves the simplicity of the original protocol but also produces excellent yields of 3,4-dihydropyridin-2(1H)-ones. Thiourea was used with similar success to provide the corresponding 3,4-dihydropyridin-2(1H)-thiones. In this case, the (+/-)-monastrol, antimitotic agent, was obtained in 92% yield and new thio analogues were synthesized.

Keywords : (+/-)-monastrol; Lewis acid; multicomponent reaction.

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