Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans

[Image: see text] 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 elect...

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Autores principales: García-Domínguez, Javier, Carranza, Marina, Jansons, Edijs, Carmona, Ana T., Robina, Inmaculada, Moreno-Vargas, Antonio J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10507663/
https://www.ncbi.nlm.nih.gov/pubmed/37616527
http://dx.doi.org/10.1021/acs.joc.3c01145
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author García-Domínguez, Javier
Carranza, Marina
Jansons, Edijs
Carmona, Ana T.
Robina, Inmaculada
Moreno-Vargas, Antonio J.
author_facet García-Domínguez, Javier
Carranza, Marina
Jansons, Edijs
Carmona, Ana T.
Robina, Inmaculada
Moreno-Vargas, Antonio J.
author_sort García-Domínguez, Javier
collection PubMed
description [Image: see text] 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.
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spelling pubmed-105076632023-09-20 Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans García-Domínguez, Javier Carranza, Marina Jansons, Edijs Carmona, Ana T. Robina, Inmaculada Moreno-Vargas, Antonio J. J Org Chem [Image: see text] 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. American Chemical Society 2023-08-24 /pmc/articles/PMC10507663/ /pubmed/37616527 http://dx.doi.org/10.1021/acs.joc.3c01145 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle García-Domínguez, Javier
Carranza, Marina
Jansons, Edijs
Carmona, Ana T.
Robina, Inmaculada
Moreno-Vargas, Antonio J.
Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans
title Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans
title_full Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans
title_fullStr Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans
title_full_unstemmed Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans
title_short Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans
title_sort transferring substituents from alkynes to furans and pyrroles through heteronorbornadienes as intermediates: synthesis of β-substituted pyrroles/furans
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10507663/
https://www.ncbi.nlm.nih.gov/pubmed/37616527
http://dx.doi.org/10.1021/acs.joc.3c01145
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