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Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26
Graphical Abstract
Scheme 1: Synthesis of 2-hetaryl-substituted 1,3-tropolones 1.
Scheme 2: Synthesis of 1,3-tropolones 7a,b and 8a,b. Reagents and conditions: method A: dioxane, reflux; meth...
Figure 1: Structural characteristics of (NH) and (OH) tautomeric forms of compounds 7 and 8 in the gas phase ...
Figure 2: Scheme of HMBC correlations of compound 7a in DMSO-d6.
Figure 3: Molecular structure of 2-(3,3-dimethyl-3H-benzo[g]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone (7b).
Figure 4: Result of matching structures of 7b (solid lines) and 2-(3,3-dimethylindolin-2-yl)-5,6,7-trichloro-...
Figure 5: Absorption and emission spectra of compound 8b in acetonitrile before (1,1’) (c 2.5 × 10−5 mol L–1)...
Scheme 3: Possible binding mode of 7 and 8 with CN− and F−.
Figure 6: Dose–response curves for H1299 and A431 cells treated with compound 7a for 24 h. *Significant diffe...
Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47
Scheme 1: Synthesis of compound 1 and N-acylated compounds 2a–c.
Figure 1: Absorption (1), fluorescence (2, λex = 410 nm) and fluorescence excitation (3, λfl = 465 nm) spectr...
Figure 2: Electronic absorption spectra of compound 2b in acetonitrile before (1) and after 15 s (2), 35 s (3...
Scheme 2: Photoisomerization of N-acylated ketoenamines 2a–c.
Figure 3: Molecular structure of O-acylated isomer 3b. Thermal ellipsoids are drawn at the 50% probability le...
Figure 4: Fragment of the molecular packing of compound 3b, showing π–π interactions in the crystalline state...
Figure 5: Absorption spectra of compound 2a in acetonitrile before (1) and after (2) the addition of Fe2+ (c2a...
Figure 6: Changes in the absorption intensity of compound 2a in acetonitrile at 520 nm after the addition of ...
Scheme 3: Sequential interaction of compounds 2a–c with Fe2+ and AcO−.
Figure 7: Job’s plot at the wavelength 429 nm, reflecting the interaction of compound 2a with Fe2+ in acetoni...
Figure 8: Fluorescence intensity of compound 2a upon alternate addition of Fe2+ and AcO−.
Beilstein J. Org. Chem. 2020, 16, 1820–1829, doi:10.3762/bjoc.16.149
Scheme 1: Photoisomerization of 2-benzo[b]thienyl fulgides.
Scheme 2: Synthesis of fulgides 3E, 3Z and fulgimides 4E, 4Z.
Scheme 3: Synthesis of fulgide 7E and fulgimide 8E.
Figure 1: Molecular structure of 3Z. Thermal ellipsoids are drawn on the 30% probability level. Selected bond...
Figure 2: Molecular structure of 3E. Thermal ellipsoids are drawn on the 30% probability level. Selected bond...
Scheme 4: Photochemical rearrangements of fulgide 3E followed by1,5-H shift.
Figure 3: Electronic absorption spectra of fulgide 3E in acetonitrile solution before (1) and after irradiati...
Figure 4: Electronic absorption spectra of fulgide 3Z in acetonitrile solution before (1) and after irradiati...
Figure 5: Molecular structure of photoproduct cis-9C’. Thermal ellipsoids are drawn on the 30% probability le...
Scheme 5: Photochemical rearrangements of fulgide 7E followed by1,5-H shift.
Figure 6: Electronic absorption spectra of fulgide 7E in acetonitrile solution before (1) and after irradiati...
Scheme 6: Photochemical rearrangements of fulgimides 4E and 8E followed by1,5-H shift.
Figure 7: Electronic absorption spectra of fulgimide 8E in acetonitrile solution before (1) and after irradia...