Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives
A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N -2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to h...
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Published in | Chemical science (Cambridge) Vol. 13; no. 35; pp. 10448 - 10454 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Cambridge
Royal Society of Chemistry
15.08.2022
The Royal Society of Chemistry |
Subjects | |
Online Access | Get full text |
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Summary: | A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of
N
-2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 These authors contributed equally to this work. |
ISSN: | 2041-6520 2041-6539 |
DOI: | 10.1039/d2sc03166c |