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Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136
Graphical Abstract
Figure 1: Selected anticancer active 3,5-diaryl-1-acylpyrazoline (left) and xanthine oxygenase inhibitors (ce...
Figure 2: Selected 1-acyl-5-hydroxypyrazolines with analgesic (left, center) and antibacterial activity (cent...
Scheme 1: Glyoxylation–alkynylation (GA) and activation–alkynylation (AA) synthesis of alkynediones in a one-...
Scheme 2: Consecutive three-component synthesis to give 5-benzoyl-3-phenyl-1H-pyrazole (6a) after alkaline de...
Figure 3: ORTEP plot of 5-benzoyl-3-phenyl-1H-pyrazole (6a) (thermal ellipsoids at 30% probability); the dire...
Scheme 3: Cyclization of 1,4-diphenylbut-3-yne-1,2-dione (3a) and Boc-hydrazine (4a) to give intermediate 5a.
Figure 4: Ellipsoid plot of 1-Boc-5-benzoyl-5-hydroxypyrazoline 5a.
Scheme 4: Model reaction for optimizing the activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hyd...
Scheme 5: One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines 5.
Figure 5: ORTEP plot and dimer of compound 5r (thermal ellipsoids at 30% probability).
Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231
Scheme 1: Mechanistic rationale and optimization of the domino synthesis of 4-arylnaphtho[2,3-c]furan-1,3-dio...
Scheme 2: Domino synthesis of 4-arylnaphtho[2,3-c]furan-1,3-diones 2 via in situ activation of arylpropiolic ...
Scheme 3: Optimization of the synthesis of 2,4-diphenyl-1H-benzo[f]isoindole-1,3(2H)-dione (4a) by imidation ...
Scheme 4: Pseudo three-component synthesis of 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones 4.
Scheme 5: Modified sequence for the synthesis of acceptor-substituted 4-aryl-1H-benzo[f]isoindole-1,3(2H)-dio...
Figure 1: The ORTEP-style plot of crystal structure 4b (ellipsoids are draw at the 40% probability level).
Scheme 6: Pseudo four-component synthesis of (E)-2,9-diphenyl-3-(phenylimino)-2,3-dihydro-1H-benzo[f]isoindol...
Scheme 7: Synthesis of 6-phenyl-12H-benzo[f]benzo[4,5]imidazo[2,1-a]isoindol-12-one (6).
Figure 2: The ORTEP-type plot of the crystal structure 5 (left) and a centrosymmetric dimer formation by π–π ...
Figure 3: The ORTEP-type plot of the asymmetric unit of the crystal structure 6 (top) and π-stacking interact...
Figure 4: Emission properties of compounds 4a,b,d–f, 5, and 6 under handheld UV-lamp (λexc ≈ 350 nm).
Figure 5: Relative emission intensities of compounds 4a,b,d–f (recorded in CH2Cl2 UVASOL® at T = 293 K; λexc ...
Figure 6: Absorption and emission properties of selected imides 4 measured in CH2Cl2 UVASOL® at 293 K with λe...
Figure 7: Hammett–Taft correlations of the emission maxima (red circles, lmax,em = 4274 · sR + 24495 [cm−1], R...
Figure 8: Relative emission intensities of the 1-phenyl-2,3-naphthaleneimide 4a (blue) and the pentacyclus 6 ...