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Synthesis of Dihydro‐5H‐Benzo[c]‐Fluorenes, Dihydroindeno[c]‐Chromenes and Thiochromenes via Intramolecular Cyclization and their Effect on Human Leukemia Cells

In this work, we describe the construction of a series of 6,7‐dihydro‐5H‐benzo[c]fluorenes. Their synthesis is based on an intramolecular‐cyclization of tricyclic substrates, which has an alcohol functional group in acidic conditions at ambient temperature. Certain reaction optimization conditions r...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-04, Vol.364 (9), p.1613-1619
Main Authors: Yan, Jun, Tran, Christine, Bignon, Jérôme, Provot, Olivier, Hamze, Abdallah
Format: Article
Language:English
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Summary:In this work, we describe the construction of a series of 6,7‐dihydro‐5H‐benzo[c]fluorenes. Their synthesis is based on an intramolecular‐cyclization of tricyclic substrates, which has an alcohol functional group in acidic conditions at ambient temperature. Certain reaction optimization conditions reveal that triflic acid was the most convenient reagent for this transformation, affording a broad range of fluorene derivatives in a 37 to 93% yield. We illustrate the robustness of this methodology through a gram‐scale synthesis, and the preparation of dihydroindeno[c]‐chromenes thiochromenes, and azulenes derivatives.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200153