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Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines
A metal‐free, photoinduced aerobic tandem amine dehydrogenation/Povarov cyclization/aromatization reaction between N‐aryl glycine esters and indoles leads to tetracyclic 11H‐indolo[3,2‐c]quinolines under mild conditions and with high yields. The reaction can be performed by using molecular iodine al...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973160/ https://www.ncbi.nlm.nih.gov/pubmed/31553081 http://dx.doi.org/10.1002/chem.201903921 |
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author | Schendera, Eva Unkel, Lisa‐Natascha Huyen Quyen, Phung Phan Salkewitz, Gwen Hoffmann, Frank Villinger, Alexander Brasholz, Malte |
author_facet | Schendera, Eva Unkel, Lisa‐Natascha Huyen Quyen, Phung Phan Salkewitz, Gwen Hoffmann, Frank Villinger, Alexander Brasholz, Malte |
author_sort | Schendera, Eva |
collection | PubMed |
description | A metal‐free, photoinduced aerobic tandem amine dehydrogenation/Povarov cyclization/aromatization reaction between N‐aryl glycine esters and indoles leads to tetracyclic 11H‐indolo[3,2‐c]quinolines under mild conditions and with high yields. The reaction can be performed by using molecular iodine along with visible light, or by combining an organic photoredox catalyst with a halide anion. Mechanistic studies reveal that product formation occurs through a combination of radical‐mediated oxidation steps with an iminium ion or N‐haloiminium ion [4+2]‐cycloaddition, and the N‐heterocyclic products constitute new analogues of the antiplasmodial natural alkaloid isocryptolepine. |
format | Online Article Text |
id | pubmed-6973160 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-69731602020-01-27 Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines Schendera, Eva Unkel, Lisa‐Natascha Huyen Quyen, Phung Phan Salkewitz, Gwen Hoffmann, Frank Villinger, Alexander Brasholz, Malte Chemistry Full Papers A metal‐free, photoinduced aerobic tandem amine dehydrogenation/Povarov cyclization/aromatization reaction between N‐aryl glycine esters and indoles leads to tetracyclic 11H‐indolo[3,2‐c]quinolines under mild conditions and with high yields. The reaction can be performed by using molecular iodine along with visible light, or by combining an organic photoredox catalyst with a halide anion. Mechanistic studies reveal that product formation occurs through a combination of radical‐mediated oxidation steps with an iminium ion or N‐haloiminium ion [4+2]‐cycloaddition, and the N‐heterocyclic products constitute new analogues of the antiplasmodial natural alkaloid isocryptolepine. John Wiley and Sons Inc. 2019-11-27 2020-01-02 /pmc/articles/PMC6973160/ /pubmed/31553081 http://dx.doi.org/10.1002/chem.201903921 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Full Papers Schendera, Eva Unkel, Lisa‐Natascha Huyen Quyen, Phung Phan Salkewitz, Gwen Hoffmann, Frank Villinger, Alexander Brasholz, Malte Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines |
title | Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines |
title_full | Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines |
title_fullStr | Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines |
title_full_unstemmed | Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines |
title_short | Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines |
title_sort | visible‐light‐mediated aerobic tandem dehydrogenative povarov/aromatization reaction: synthesis of isocryptolepines |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973160/ https://www.ncbi.nlm.nih.gov/pubmed/31553081 http://dx.doi.org/10.1002/chem.201903921 |
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