Authors: | Tymann, Dina Christina Benedix, Lars Iovkova, Lyuba Pallach, Roman Henke, Sebastian Tymann, David Hiersemann, Martin |
Title: | Photochemical approach to the cyclohepta[b]indole scaffold by annulative two-carbon ring-expansion |
Language (ISO): | en |
Abstract: | 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. |
Subject Headings: | Cascade reactions Cyclohepta[b]indole Indole[2,3-d]tropone Photochemistry Ring expansion |
URI: | http://hdl.handle.net/2003/40326 http://dx.doi.org/10.17877/DE290R-22201 |
Issue Date: | 2020-05-28 |
Rights link: | https://creativecommons.org/licenses/by/4.0/ |
Appears in Collections: | Organische Chemie |
Files in This Item:
File | Description | Size | Format | |
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chem.202002581.pdf | 1.2 MB | Adobe PDF | View/Open |
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