Synthesis of monastrol and of new biginelli compounds promoted by in(otf)3
| Autor: | Paola S. Machado, Dennis Russowsky, Marla Narciso Godoi, Hellen S. Costenaro, Eliane Kramer, Marcelo Gonçalves Montes D'Oca |
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| Jazyk: | portugalština |
| Rok vydání: | 2005 |
| Předmět: | |
| Zdroj: | Química Nova v.28 n.6 2005 Química Nova Sociedade Brasileira de Química (SBQ) instacron:SBQ Repositório Institucional da UFRGS Universidade Federal do Rio Grande do Sul (UFRGS) instacron:UFRGS |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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