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

• Autor(a) principal: Godoi,Marla N.
• Data de Publicação: 2005
• Outros Autores: Costenaro,Hellen S., Kramer,Eliane, Machado,Paola S., D'Oca,Marcelo G. Montes, Russowsky,Dennis
• Tipo de documento: Artigo
• Idioma: por
• Título da fonte: Química Nova (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422005000600015
• topic: (+/-)-monastrol; Lewis acid; multicomponent reaction

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.