TY  - DATA
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5846
AB  - We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09–0.81.
PB  - Royal Society of Chemistry
T2  - Organic & Biomolecular Chemistry
T1  - Supplementary material for: Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/D2OB02119F
VL  - 21
IS  - 6
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5846
ER  - 

@misc{
author = "Aleksić, Jovana and Stojanović, Milovan and Bošković, Jakša and Baranac-Stojanović, Marija",
abstract = "We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09–0.81.",
publisher = "Royal Society of Chemistry",
journal = "Organic & Biomolecular Chemistry",
title = "Supplementary material for: Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/D2OB02119F",
volume = "21",
number = "6",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5846"
}

Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M..Supplementary material for: Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/D2OB02119F. in Organic & Biomolecular Chemistry
Royal Society of Chemistry., 21(6).
https://hdl.handle.net/21.15107/rcub_cherry_5846

Aleksić J, Stojanović M, Bošković J, Baranac-Stojanović M. Supplementary material for: Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/D2OB02119F. in Organic & Biomolecular Chemistry.21(6).
https://hdl.handle.net/21.15107/rcub_cherry_5846 .

Aleksić, Jovana, Stojanović, Milovan, Bošković, Jakša, Baranac-Stojanović, Marija, "Supplementary material for: Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/D2OB02119F" in Organic & Biomolecular Chemistry, 21, no. 6,
https://hdl.handle.net/21.15107/rcub_cherry_5846 .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5820
AB  - We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09–0.81.
PB  - Royal Society of Chemistry
T2  - Organic & Biomolecular Chemistry
T1  - Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines
VL  - 21
IS  - 6
SP  - 1187
EP  - 1205
DO  - 10.1039/D2OB02119F
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Bošković, Jakša and Baranac-Stojanović, Marija",
year = "2023",
abstract = "We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09–0.81.",
publisher = "Royal Society of Chemistry",
journal = "Organic & Biomolecular Chemistry",
title = "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines",
volume = "21",
number = "6",
pages = "1187-1205",
doi = "10.1039/D2OB02119F"
}

Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/D2OB02119F

Aleksić J, Stojanović M, Bošković J, Baranac-Stojanović M. Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry. 2023;21(6):1187-1205.
doi:10.1039/D2OB02119F .

Aleksić, Jovana, Stojanović, Milovan, Bošković, Jakša, Baranac-Stojanović, Marija, "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines" in Organic & Biomolecular Chemistry, 21, no. 6 (2023):1187-1205,
https://doi.org/10.1039/D2OB02119F . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6106
AB  - We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09–0.81.
T2  - Organic & Biomolecular Chemistry
T1  - Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines
VL  - 21
IS  - 6
SP  - 1187
EP  - 1205
DO  - 10.1039/D2OB02119F
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Bošković, Jakša and Baranac-Stojanović, Marija",
year = "2023",
abstract = "We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09–0.81.",
journal = "Organic & Biomolecular Chemistry",
title = "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines",
volume = "21",
number = "6",
pages = "1187-1205",
doi = "10.1039/D2OB02119F"
}

Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry, 21(6), 1187-1205.
https://doi.org/10.1039/D2OB02119F

Aleksić J, Stojanović M, Bošković J, Baranac-Stojanović M. Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry. 2023;21(6):1187-1205.
doi:10.1039/D2OB02119F .

Aleksić, Jovana, Stojanović, Milovan, Bošković, Jakša, Baranac-Stojanović, Marija, "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines" in Organic & Biomolecular Chemistry, 21, no. 6 (2023):1187-1205,
https://doi.org/10.1039/D2OB02119F . .

TY  - THES
AU  - Bošković, Jakša
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5580
AB  - U okviru ovog master rada ispitana je mogućnost dobijanja model jedinjenja u kome je C60 funkcionalizovan podjedinicom koja sadrži fenolni segment. Kao fenolna komponenta korišćena je m-hidroksibenzoeva kiselina, koja je za fuleren vezana preko pirolidinskog jezgra, koje nastaje [3+2]-cikloadicijom. Dalji cilj istraživanja je povezivanje fulerena sa strukturama koje imaju jako antioksidativno dejstvo (galna kiselina, polifenoli).
T1  - Sinteza fenolnih estara fuleropirolidina
SP  - 3
EP  - 49
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5580
ER  - 

@mastersthesis{
author = "Bošković, Jakša",
year = "2022",
abstract = "U okviru ovog master rada ispitana je mogućnost dobijanja model jedinjenja u kome je C60 funkcionalizovan podjedinicom koja sadrži fenolni segment. Kao fenolna komponenta korišćena je m-hidroksibenzoeva kiselina, koja je za fuleren vezana preko pirolidinskog jezgra, koje nastaje [3+2]-cikloadicijom. Dalji cilj istraživanja je povezivanje fulerena sa strukturama koje imaju jako antioksidativno dejstvo (galna kiselina, polifenoli).",
title = "Sinteza fenolnih estara fuleropirolidina",
pages = "3-49",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5580"
}

Bošković, J.. (2022). Sinteza fenolnih estara fuleropirolidina. , 3-49.
https://hdl.handle.net/21.15107/rcub_cherry_5580

Bošković J. Sinteza fenolnih estara fuleropirolidina. 2022;:3-49.
https://hdl.handle.net/21.15107/rcub_cherry_5580 .

Bošković, Jakša, "Sinteza fenolnih estara fuleropirolidina" (2022):3-49,
https://hdl.handle.net/21.15107/rcub_cherry_5580 .

TY  - THES
AU  - Bošković, Jakša
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4691
AB  - U okviru ovog diplomskog rada ispitana je mogućnost dobijanja hidroksiestara fulerena reakcijom 1,2–adicije karboksilnih kiselina na fuleren C60, u prisustvu gvožđe(III)-hlorida kao katalizatora. Kao potencijalni supstrati korišćeni su galna kiselina, kao i njeni THP- i alkiloksi-derivati. Rezultati su pokazali da pod primenjenim uslovima ne dolazi do 1,2–adicije, te da ova metoda nije pogodna za željenu sintezu
T1  - Reaktivnost galne kiseline i njenih derivata u 1,2-adicijama na fuleren C60
SP  - 4
EP  - 45
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4691
ER  - 

@misc{
author = "Bošković, Jakša",
year = "2021",
abstract = "U okviru ovog diplomskog rada ispitana je mogućnost dobijanja hidroksiestara fulerena reakcijom 1,2–adicije karboksilnih kiselina na fuleren C60, u prisustvu gvožđe(III)-hlorida kao katalizatora. Kao potencijalni supstrati korišćeni su galna kiselina, kao i njeni THP- i alkiloksi-derivati. Rezultati su pokazali da pod primenjenim uslovima ne dolazi do 1,2–adicije, te da ova metoda nije pogodna za željenu sintezu",
title = "Reaktivnost galne kiseline i njenih derivata u 1,2-adicijama na fuleren C60",
pages = "4-45",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4691"
}

Bošković, J.. (2021). Reaktivnost galne kiseline i njenih derivata u 1,2-adicijama na fuleren C60. , 4-45.
https://hdl.handle.net/21.15107/rcub_cherry_4691

Bošković J. Reaktivnost galne kiseline i njenih derivata u 1,2-adicijama na fuleren C60. 2021;:4-45.
https://hdl.handle.net/21.15107/rcub_cherry_4691 .

Bošković, Jakša, "Reaktivnost galne kiseline i njenih derivata u 1,2-adicijama na fuleren C60" (2021):4-45,
https://hdl.handle.net/21.15107/rcub_cherry_4691 .