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Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion
We report on the implementation of the concept of a photochemically elicited two‐carbon homologation of a π‐donor–π‐acceptor substituted chromophore by triple‐bond insertion. Implementing a phenyl connector between the slide‐in module and the chromophore enabled the synthesis of cylohepta[b]indole‐t...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540574/ https://www.ncbi.nlm.nih.gov/pubmed/32463529 http://dx.doi.org/10.1002/chem.202002581 |
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author | Tymann, Dina Christina Benedix, Lars Iovkova, Lyuba Pallach, Roman Henke, Sebastian Tymann, David Hiersemann, Martin |
author_facet | Tymann, Dina Christina Benedix, Lars Iovkova, Lyuba Pallach, Roman Henke, Sebastian Tymann, David Hiersemann, Martin |
author_sort | Tymann, Dina Christina |
collection | PubMed |
description | We report on the implementation of the concept of a photochemically elicited two‐carbon homologation of a π‐donor–π‐acceptor substituted chromophore by triple‐bond insertion. Implementing a phenyl connector between the slide‐in module and the chromophore enabled the synthesis of cylohepta[b]indole‐type building blocks by a metal‐free annulative one‐pot two‐carbon ring expansion of the five‐membered chromophore. Post‐irradiative structural elaboration provided founding members of the indolo[2,3‐d]tropone family of compounds. Control experiments in combination with computational chemistry on this multibond reorganization process founded the basis for a mechanistic hypothesis. |
format | Online Article Text |
id | pubmed-7540574 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-75405742020-10-15 Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion Tymann, Dina Christina Benedix, Lars Iovkova, Lyuba Pallach, Roman Henke, Sebastian Tymann, David Hiersemann, Martin Chemistry Communications We report on the implementation of the concept of a photochemically elicited two‐carbon homologation of a π‐donor–π‐acceptor substituted chromophore by triple‐bond insertion. Implementing a phenyl connector between the slide‐in module and the chromophore enabled the synthesis of cylohepta[b]indole‐type building blocks by a metal‐free annulative one‐pot two‐carbon ring expansion of the five‐membered chromophore. Post‐irradiative structural elaboration provided founding members of the indolo[2,3‐d]tropone family of compounds. Control experiments in combination with computational chemistry on this multibond reorganization process founded the basis for a mechanistic hypothesis. John Wiley and Sons Inc. 2020-08-17 2020-09-16 /pmc/articles/PMC7540574/ /pubmed/32463529 http://dx.doi.org/10.1002/chem.202002581 Text en © 2020 The Authors. Published by Wiley-VCH GmbH 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 | Communications Tymann, Dina Christina Benedix, Lars Iovkova, Lyuba Pallach, Roman Henke, Sebastian Tymann, David Hiersemann, Martin Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion |
title | Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion |
title_full | Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion |
title_fullStr | Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion |
title_full_unstemmed | Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion |
title_short | Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two‐Carbon Ring‐Expansion |
title_sort | photochemical approach to the cyclohepta[b]indole scaffold by annulative two‐carbon ring‐expansion |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540574/ https://www.ncbi.nlm.nih.gov/pubmed/32463529 http://dx.doi.org/10.1002/chem.202002581 |
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