Síntese do monastrol e novos compostos de Biginelli promovida por In(OTf)3

AUTOR(ES)

Godoi, Marla N., Costenaro, Hellen S., Kramer, Eliane, Machado, Paola S., D'Oca, Marcelo G. Montes, Russowsky, Dennis

FONTE

Química Nova

DATA DE PUBLICAÇÃO

2005-12

RESUMO

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.

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