Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
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 modif...
| Authors: | , , , , , |
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| Format: | article |
| Status: | Published version |
| Publication Date: | 2005 |
| Country: | Brasil |
| Institution: | Universidade Federal do Rio Grande do Sul (UFRGS) |
| Repository: | Repositório Institucional da UFRGS |
| Language: | Portuguese |
| OAI Identifier: | oai:www.lume.ufrgs.br:10183/72847 |
| Online Access: | http://hdl.handle.net/10183/72847 |
| Access Level: | Open access |
| Keyword: | Síntese orgânica Monastrol (+/-)-monastrol Lewis acid Multicomponent reaction |
| Summary: | 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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