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3 article(s) from Marinić, Željko

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

Dragana Vuk,
Irena Škorić,
Valentina Milašinović,
Krešimir Molčanov and
Željko Marinić

Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

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Figure 1: Known biologically active bicyclo[3.2.1]octenes/octadienes.

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Figure 2: Previously prepared bicyclo[3.2.1]octenes/octadienes with cholinesterase inhibitory properties.

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Scheme 1: Synthesis of annulated furobenzobicyclo[3.2.1]octadiene compounds.

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Scheme 2: Synthesis of annulated thiophenebicyclo[3.2.1]octadiene compounds 8-10.

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Scheme 3: Synthesis of compound 11.

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Figure 3: ¹H NMR spectra (CDCl₃) for the trans-isomers 3–6.

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Figure 4: UV spectra in ethanol (95%) of the cis- and trans-isomers of compound 3.

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Figure 5: Photolysis spectra of cis-3 (a) and trans-3 (b) in ethanol (95%).

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Figure 6: UV spectra in ethanol (95%) of the trans-isomers of compounds 3–7.

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Figure 7: Molecular structure of compound trans-6. Displacement ellipsoids are drawn for the probability of 3...

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Figure 8: Crystal packing of trans-6. (a) Chain parallel to [100] and (b) chain parallel to [010].

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Figure 9: ¹H NMR spectra (CDCl₃) of compounds 1, 8, and 9.

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Scheme 4: Synthesis of compound 12.

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Figure 10: UV spectra of compounds 1 and 12 in ethanol (95%).

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Figure 11: Photolysis spectra of compound 12 in ethanol (95%).

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Scheme 5: Possible outcomes of future photocatalytic oxygenation reactions of new benzobicyclo[3.2.1.]octadie...

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Published 22 May 2020

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Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles

Ivana Šagud,
Simona Božić,
Željko Marinić and
Marija Šindler-Kulyk

Beilstein J. Org. Chem. 2014, 10, 2222–2229, doi:10.3762/bjoc.10.230

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Scheme 1: Synthesis of 4- (1) and 5-(2-vinylstyryl)oxazoles (2).

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Scheme 2: Irradiation of 4- (1) and 5-(2-vinylstyryl)oxazoles (2) (crude reaction mixtures).

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Figure 1: Part of ¹H NMR spectra in C₆D₆ of the crude photomixtures after 200 min (300 nm, rt ) of irradiatio...

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Scheme 3: Plausible mechanisms of oxazoline ring-opening in photoproduct 10.

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Figure 2: ¹H NMR spectra in C₆D₆ of rel-(9S)-12a (a) and rel-(9S)-11 (b).

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Scheme 4: Mechanism of the formation of polycyclic compounds (8–10).

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Scheme 5: Reactions of the photochemical product 8 with EtOH, MeOD and H₂O/silica gel.

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Scheme 6: Plausible mechanisms of oxazoline ring opening in photoproduct 10 and formation of 12.

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Published 18 Sep 2014

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Photochemical and thermal intramolecular 1,3-dipolar cycloaddition reactions of new o-stilbene-methylene-3-sydnones and their synthesis

Kristina Butković,
Željko Marinić,
Krešimir Molčanov,
Biserka Kojić-Prodić and
Marija Šindler-Kulyk

Beilstein J. Org. Chem. 2011, 7, 1663–1670, doi:10.3762/bjoc.7.196

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Figure 1: Resonance structures of the sydnone ring.

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Scheme 1: Thermal and photochemical intermolecular [3 + 2] cycloadditions.

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Figure 2: Illustration of intramolecular [3 + 2] cycloadditions.

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Figure 3: Styryl-sydnone 1 and stilbenyl sydnone 2 and their photoproducts F and G, respectively; target mole...

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Scheme 2: Synthesis of the target molecules 3a and 3b.

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Scheme 3: Photolysis of cis- or trans-3.

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Scheme 4: Aromatization with DDQ.

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Scheme 5: Possible mechanism for the formation of the photoproducts.

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Scheme 6: Thermal reaction of trans-3.

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Figure 4: ORTEP of compound 14.

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Scheme 7: Thermal reaction of cis-3.

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Figure 5: Proposed stereochemical pathway of sydnone ring (CH–N) and trans- and cis-stilbene (α–β).

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Figure 6: Proposed stereochemical pathway of sydnone ring (N–CH) and trans- and cis-stilbene (α–β).

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Scheme 8: Possible formation of thermal products 14 (from trans-3) and 15 (from cis-3).

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Published 13 Dec 2011

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