TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5681
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  - Great Britain : Royal Society of Chemistry
T2  - Organic & Biomolecular Chemistry
T1  - Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines
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 = "Great Britain : Royal Society of Chemistry",
journal = "Organic & Biomolecular Chemistry",
title = "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines",
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
Great Britain : Royal Society of Chemistry..
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;.
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 (2023),
https://doi.org/10.1039/d2ob02119f . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5790
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 . .