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3 article(s) from Reiss, Guido J

Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B

Horst Weber,
Kim-Thao Tran-Cong,
Bernhard Mayer,
Guido J. Reiss,
Iryna S. Konovalova,
Marc S. Appelhans,
Kenneth R. Wood and
Claus M. Passreiter

Beilstein J. Org. Chem. 2026, 22, 535–546, doi:10.3762/bjoc.22.39

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Figure 1: Structures of isomeric melifoliones and corresponding oxidation products.

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Scheme 1: Synthesis of melifoliones and by-products: a) pyridine/60 °C/8 h/51%, b) microwave/140 °C/20 min/70...

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Figure 2: Structure of iodized melifoliones.

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Scheme 2: Reaction of melifolione A (1) with iodosobenzene diacetate.

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Scheme 3: Hypothetical pathway for the oxidative ring contraction of melifolione A (1) with ferricyanide/hydr...

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Figure 3: Left Part: 11 (main fraction); Right part: 12 (side product).

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Scheme 4: Oxidative ring contraction of melifolione B (2).

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Scheme 5: Alternative routes to the spirofuranones 11 and 12 via hypothetical pyranone epoxides 13 and 14.

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Published 24 Mar 2026

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One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

Christina Görgen,
Katharina Boden,
Guido J. Reiss,
Walter Frank and
Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136

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Figure 1: Selected anticancer active 3,5-diaryl-1-acylpyrazoline (left) and xanthine oxygenase inhibitors (ce...

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Figure 2: Selected 1-acyl-5-hydroxypyrazolines with analgesic (left, center) and antibacterial activity (cent...

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Scheme 1: Glyoxylation–alkynylation (GA) and activation–alkynylation (AA) synthesis of alkynediones in a one-...

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Scheme 2: Consecutive three-component synthesis to give 5-benzoyl-3-phenyl-1H-pyrazole (6a) after alkaline de...

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Figure 3: ORTEP plot of 5-benzoyl-3-phenyl-1H-pyrazole (6a) (thermal ellipsoids at 30% probability); the dire...

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Scheme 3: Cyclization of 1,4-diphenylbut-3-yne-1,2-dione (3a) and Boc-hydrazine (4a) to give intermediate 5a.

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Figure 4: Ellipsoid plot of 1-Boc-5-benzoyl-5-hydroxypyrazoline 5a.

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Scheme 4: Model reaction for optimizing the activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hyd...

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Scheme 5: One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines 5.

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Figure 5: ORTEP plot and dimer of compound 5r (thermal ellipsoids at 30% probability).

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Published 19 Jun 2019

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One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

Melanie Denißen,
Alexander Kraus,
Guido J. Reiss and
Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

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Scheme 1: Mechanistic rationale and optimization of the domino synthesis of 4-arylnaphtho[2,3-c]furan-1,3-dio...

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Scheme 2: Domino synthesis of 4-arylnaphtho[2,3-c]furan-1,3-diones 2 via in situ activation of arylpropiolic ...

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Scheme 3: Optimization of the synthesis of 2,4-diphenyl-1H-benzo[f]isoindole-1,3(2H)-dione (4a) by imidation ...

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Scheme 4: Pseudo three-component synthesis of 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones 4.

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Scheme 5: Modified sequence for the synthesis of acceptor-substituted 4-aryl-1H-benzo[f]isoindole-1,3(2H)-dio...

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Figure 1: The ORTEP-style plot of crystal structure 4b (ellipsoids are draw at the 40% probability level).

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Scheme 6: Pseudo four-component synthesis of (E)-2,9-diphenyl-3-(phenylimino)-2,3-dihydro-1H-benzo[f]isoindol...

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Scheme 7: Synthesis of 6-phenyl-12H-benzo[f]benzo[4,5]imidazo[2,1-a]isoindol-12-one (6).

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Figure 2: The ORTEP-type plot of the crystal structure 5 (left) and a centrosymmetric dimer formation by π–π ...

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Figure 3: The ORTEP-type plot of the asymmetric unit of the crystal structure 6 (top) and π-stacking interact...

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Figure 4: Emission properties of compounds 4a,b,d–f, 5, and 6 under handheld UV-lamp (λ_exc ≈ 350 nm).

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Figure 5: Relative emission intensities of compounds 4a,b,d–f (recorded in CH₂Cl₂ UVASOL^® at T = 293 K; λ_exc ...

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Figure 6: Absorption and emission properties of selected imides 4 measured in CH₂Cl₂ UVASOL^® at 293 K with λ_e...

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Figure 7: Hammett–Taft correlations of the emission maxima (red circles, l_max,em = 4274 · s_R + 24495 [cm⁻¹], R...

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Figure 8: Relative emission intensities of the 1-phenyl-2,3-naphthaleneimide 4a (blue) and the pentacyclus 6 ...

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Published 03 Nov 2017

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Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B

One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P® activation of 3-arylpropiolic acids

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids