Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two-Carbon Ring-Expansion |
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Authors: | Dr Dina Christina Tymann Lars Benedix Dr Lyuba Iovkova Roman Pallach Prof Dr Sebastian Henke Dr David Tymann Prof Dr Martin Hiersemann |
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Institution: | Fakultät für Chemie und Chemische Biologie, TU Dortmund, 44227 Dortmund, Germany |
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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 cyloheptab]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 indolo2,3-d]tropone family of compounds. Control experiments in combination with computational chemistry on this multibond reorganization process founded the basis for a mechanistic hypothesis. |
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Keywords: | cascade reactions cyclohepta[b]indole indole[2 3-d]tropone photochemistry ring expansion |
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