Synthesis of 5-alkynyl-2,2,6-trimethyl-1,3-dioxin-4-ones and 1,4-disubstituted-1,2,3-triazoles
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
19/10/2012
19/10/2012
2011
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| Resumo |
Herein we report an approach to the formation of 5-alkynyl-1,3-dioxin-4-ones using Suzuki-Miyaura cross-coupling reaction of potassium alkynyltrifluoroborate salts with 2,2,6-trimethy1-5-iodo-1,3-dioxin-4-one. The resulting 5-ethynyltrimethylsilyl-1,3-dioxin-4-ones obtained through the Sonogashira reaction were further reacted in a Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition to form functionalized 1,4-disubstituted-1,2,3-triazoles in good yields, using mild conditions and ultrasonic radiation to expedite the reaction. (C) 2011 Elsevier Ltd. All rights reserved. Conselho Nacional de Desenvolvimento Cientifico e Tecnologico[CNPq 300.613/2007-5] Fundacao de Amparo a Pesquisa do Estado de Sao Paulo[FAPESP 06/50190-7] FAPESP Fundacao de Amparo a Pesquisa do Estado de Sao Paulo[07/02382-7] FAPESP Fundacao de Amparo a Pesquisa do Estado de Sao Paulo[07/59404-2] |
| Identificador |
TETRAHEDRON LETTERS, v.52, n.33, p.4256-4261, 2011 0040-4039 http://producao.usp.br/handle/BDPI/20412 10.1016/j.tetlet.2011.04.072 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
| Relação |
Tetrahedron Letters |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #Suzuki-Miyaura #2,2,6-Trimethyl-5-iodo-1,3-dioxin-4-one #Alkynyltrifluoroborates #Cross-coupling reaction #1,4-Disubstituted-1,2,3-triazoles #AZIDE-ALKYNE CYCLOADDITION #CROSS-COUPLING REACTIONS #N-ACYLIMINIUM IONS #CLICK CHEMISTRY #ORGANIC-SYNTHESIS #STEREOSELECTIVE-SYNTHESIS #NUCLEOPHILIC-ADDITION #MATERIAL SCIENCE #POTASSIUM #SALTS #Chemistry, Organic |
| Tipo |
article original article publishedVersion |
