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DOI: 10.1055/a-1677-4881
An Oxidant- and Catalyst-Free Synthesis of Dibenzo[a,c]carbazoles via UV Light Irradiation of 2,3-Diphenyl-1H-indoles
We are grateful for financial support from the National Natural Science Foundation of China (No. 21672132).
Abstract
An efficient methodology for the synthesis of dibenzo[a,c]carbazoles via annulation of 2,3-diphenyl-1H-indoles in EtOH under UV light irradiation (λ = 365 nm) along with hydrogen evolution is described. This method exhibits the advantages of mild reaction conditions, no requirement of any oxidants and catalysts, and release of hydrogen as the only byproduct. Notably, the mechanism investigation confirms that the trans-4b,8a-dihydro-9H-dibenzo[a,c]carbazole intermediate could convert into cis-4b,8a-dihydro-9H-dibenzo[a,c]carbazole, which relies on the nitrogen atom of the indole ring. This is followed by intramolecular dehydrogenation which yields the dibenzo[a,c]carbazoles.
Key words
photocyclization - 2,3-diphenyl-1H-indoles - hydrogen evolution - [1,5]-H shift - dibenzo[a,c]carbazolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1677-4881.
- Supporting Information
Publikationsverlauf
Eingereicht: 02. September 2021
Angenommen nach Revision: 23. Oktober 2021
Accepted Manuscript online:
23. Oktober 2021
Artikel online veröffentlicht:
30. November 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
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