Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes

[Image: see text] An alkylation/olefination cascade of indolecarboxaldehydes and phosphonate-functionalized donor–acceptor cyclopropanes affords functionalized dihydrocarbazoles and cyclohepta[cd]indoles in formal (3 + 3) and (4 + 3) cycloadditions. A minor modification to the reaction conditions al...

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Autores principales: Faltracco, Matteo, Damian, Matteo, Ruijter, Eelco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8491164/
https://www.ncbi.nlm.nih.gov/pubmed/34543040
http://dx.doi.org/10.1021/acs.orglett.1c02795
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author Faltracco, Matteo
Damian, Matteo
Ruijter, Eelco
author_facet Faltracco, Matteo
Damian, Matteo
Ruijter, Eelco
author_sort Faltracco, Matteo
collection PubMed
description [Image: see text] An alkylation/olefination cascade of indolecarboxaldehydes and phosphonate-functionalized donor–acceptor cyclopropanes affords functionalized dihydrocarbazoles and cyclohepta[cd]indoles in formal (3 + 3) and (4 + 3) cycloadditions. A minor modification to the reaction conditions also allows access to the fully aromatic heterocyclic scaffolds by thermal loss of an electron-rich aryl moiety.
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spelling pubmed-84911642021-10-05 Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes Faltracco, Matteo Damian, Matteo Ruijter, Eelco Org Lett [Image: see text] An alkylation/olefination cascade of indolecarboxaldehydes and phosphonate-functionalized donor–acceptor cyclopropanes affords functionalized dihydrocarbazoles and cyclohepta[cd]indoles in formal (3 + 3) and (4 + 3) cycloadditions. A minor modification to the reaction conditions also allows access to the fully aromatic heterocyclic scaffolds by thermal loss of an electron-rich aryl moiety. American Chemical Society 2021-09-20 2021-10-01 /pmc/articles/PMC8491164/ /pubmed/34543040 http://dx.doi.org/10.1021/acs.orglett.1c02795 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Faltracco, Matteo
Damian, Matteo
Ruijter, Eelco
Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes
title Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes
title_full Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes
title_fullStr Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes
title_full_unstemmed Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes
title_short Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes
title_sort synthesis of carbazoles and dihydrocarbazoles by a divergent cascade reaction of donor–acceptor cyclopropanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8491164/
https://www.ncbi.nlm.nih.gov/pubmed/34543040
http://dx.doi.org/10.1021/acs.orglett.1c02795
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