“…[9] Despite the high interest in their scaffolds, DHBFs are less studied than THBFs, possibly due to their assumed lower chemical stability. [10] Nevertheless, some synthetic strategies have been developed to conceive these types of heterocyclic compounds during the last decades.…”
In this work, we describe the construction of a series of 6,7-dihydro-5Hbenzo[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.
“…[9] Despite the high interest in their scaffolds, DHBFs are less studied than THBFs, possibly due to their assumed lower chemical stability. [10] Nevertheless, some synthetic strategies have been developed to conceive these types of heterocyclic compounds during the last decades.…”
In this work, we describe the construction of a series of 6,7-dihydro-5Hbenzo[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.
A New Synthesis of Benzo(c)fluorene-Structures.--(FIES, M.; STROBEL, M.; FRIEDRICH, K.; J. Prakt. Chem./Chem. -Ztg. 338 (1996) 6, 581-582; Inst. Org. Chem. Biochem., Univ. Freiburg, D-79104 Freiburg/Br., Germany; EN)
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