Artículo
Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans
Autor/es | García Domínguez, Javier
Carranza César, Marina Jansons, Edijs Carmona Asenjo, Ana Teresa Robina Ramírez, Inmaculada Moreno Vargas, Antonio José |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2023 |
Fecha de depósito | 2023-11-02 |
Publicado en |
|
Resumen | The use of 7-oxa/azanorbornadienes as synthetic intermediates for the preparation of 3/4-substituted (β-substituted) furans/pyrroles is presented. The method lies in the inverse electron demand Diels-Alder (iEDDA) cycloaddition ... The use of 7-oxa/azanorbornadienes as synthetic intermediates for the preparation of 3/4-substituted (β-substituted) furans/pyrroles is presented. The method lies in the inverse electron demand Diels-Alder (iEDDA) cycloaddition between a substituted heteronorbornadiene and an electron-poor tetrazine followed by spontaneous fragmentation of the resulting cycloadduct via two retro-Diels-Alder (rDA) reactions affording a β-substituted furan/pyrrole. The scope of this tandem iEDDA/rDA/rDA reaction was explored in the preparation of 29 heterocycles. A one-pot procedure starting directly from the alkyne precursors of the heteronorbornadiene intermediates is also described. |
Agencias financiadoras | Ministerio de Ciencia e Innovación (MICIN). España Junta de Andalucía |
Identificador del proyecto | PID2020-116460RB-100
P20-00532 |
Cita | García Domínguez, J., Carranza César, M., Jansons, E., Carmona Asenjo, A.T., Robina Ramírez, I. y Moreno Vargas, A.J. (2023). Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans. Journal of Organic Chemistry, 88 (18), 13331-13338. https://doi.org/10.1021/acs.joc.3c01145. |
Ficheros | Tamaño | Formato | Ver | Descripción |
---|---|---|---|---|
Transferring Substituents.pdf | 1.913Mb | [PDF] | Ver/ | |