Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations

[Image: see text] The synthesis of cyclohepta[b]indole derivatives through the dearomative (4 + 3) cycloaddition reaction of 2-vinylindoles or 4H-furo[3,2-b]indoles with in situ generated oxyallyl cations is reported. Oxyallyl cations are generated from α-bromoketones in the presence of a base and a...

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Autores principales: Pirovano, Valentina, Brambilla, Elisa, Moretti, Andrea, Rizzato, Silvia, Abbiati, Giorgio, Nava, Donatella, Rossi, Elisabetta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7997566/
https://www.ncbi.nlm.nih.gov/pubmed/31975604
http://dx.doi.org/10.1021/acs.joc.9b03117
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author Pirovano, Valentina
Brambilla, Elisa
Moretti, Andrea
Rizzato, Silvia
Abbiati, Giorgio
Nava, Donatella
Rossi, Elisabetta
author_facet Pirovano, Valentina
Brambilla, Elisa
Moretti, Andrea
Rizzato, Silvia
Abbiati, Giorgio
Nava, Donatella
Rossi, Elisabetta
author_sort Pirovano, Valentina
collection PubMed
description [Image: see text] The synthesis of cyclohepta[b]indole derivatives through the dearomative (4 + 3) cycloaddition reaction of 2-vinylindoles or 4H-furo[3,2-b]indoles with in situ generated oxyallyl cations is reported. Oxyallyl cations are generated from α-bromoketones in the presence of a base and a perfluorinated solvent. Cyclohepta[b]indole scaffolds are obtained under mild reaction conditions, in the absence of expensive catalysts, starting from simple reagents, in good to excellent yields and with complete diasteroselectivity. Preliminary expansion of the scope to 3-vinylindoles and to aza-oxyallyl cations is reported.
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spelling pubmed-79975662021-03-29 Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations Pirovano, Valentina Brambilla, Elisa Moretti, Andrea Rizzato, Silvia Abbiati, Giorgio Nava, Donatella Rossi, Elisabetta J Org Chem [Image: see text] The synthesis of cyclohepta[b]indole derivatives through the dearomative (4 + 3) cycloaddition reaction of 2-vinylindoles or 4H-furo[3,2-b]indoles with in situ generated oxyallyl cations is reported. Oxyallyl cations are generated from α-bromoketones in the presence of a base and a perfluorinated solvent. Cyclohepta[b]indole scaffolds are obtained under mild reaction conditions, in the absence of expensive catalysts, starting from simple reagents, in good to excellent yields and with complete diasteroselectivity. Preliminary expansion of the scope to 3-vinylindoles and to aza-oxyallyl cations is reported. American Chemical Society 2020-01-24 2020-03-06 /pmc/articles/PMC7997566/ /pubmed/31975604 http://dx.doi.org/10.1021/acs.joc.9b03117 Text en 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 Pirovano, Valentina
Brambilla, Elisa
Moretti, Andrea
Rizzato, Silvia
Abbiati, Giorgio
Nava, Donatella
Rossi, Elisabetta
Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations
title Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations
title_full Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations
title_fullStr Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations
title_full_unstemmed Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations
title_short Synthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations
title_sort synthesis of cyclohepta[b]indoles by (4 + 3) cycloaddition of 2-vinylindoles or 4h-furo[3,2-b]indoles with oxyallyl cations
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7997566/
https://www.ncbi.nlm.nih.gov/pubmed/31975604
http://dx.doi.org/10.1021/acs.joc.9b03117
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