Bugarinović, Jovana

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  • Bugarinović, Jovana (4)
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Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction

Stevanović, Dragana D.; Bugarinović, Jovana; Pešić, Marko; Todosijević, Anka; Bogdanović, Goran A.; Damljanović, Ivan S.

(2021)

TY  - JOUR
AU  - Stevanović, Dragana D.
AU  - Bugarinović, Jovana
AU  - Pešić, Marko
AU  - Todosijević, Anka
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10070
AB  - A simple protocol has been developed for the chemoselective synthesis of ferrocene-containing Rauhut–Currier adducts from 1-ferrocenyl-2-nitroethene and vinyl ketones using 20 mol% of triphenylphosphine. Multifunctional ferrocene derivatives were obtained in moderate to high yields (51–92%) by the coupling between the α-position of vinyl ketones and the β-position of the nitroalkene. The study of the Rauhut–Currier reaction under the described conditions showed that the strong electron-donating group at the β-position of nitroalkenes plays a significant role in the reaction outcome due to prevention of polymerization and stabilization of the zwitterionic intermediate. Additionally, a preparative synthesis of 4-ferrocenyl-3-methylene-5-nitropentan-2-one was carried out and its synthetic transformations showed easy conversion to other useful building blocks.
T2  - RSC Advances
T1  - Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction
VL  - 11
IS  - 57
SP  - 36208
EP  - 36214
DO  - 10.1039/D1RA07619A
ER  - 
@article{
author = "Stevanović, Dragana D. and Bugarinović, Jovana and Pešić, Marko and Todosijević, Anka and Bogdanović, Goran A. and Damljanović, Ivan S.",
year = "2021",
abstract = "A simple protocol has been developed for the chemoselective synthesis of ferrocene-containing Rauhut–Currier adducts from 1-ferrocenyl-2-nitroethene and vinyl ketones using 20 mol% of triphenylphosphine. Multifunctional ferrocene derivatives were obtained in moderate to high yields (51–92%) by the coupling between the α-position of vinyl ketones and the β-position of the nitroalkene. The study of the Rauhut–Currier reaction under the described conditions showed that the strong electron-donating group at the β-position of nitroalkenes plays a significant role in the reaction outcome due to prevention of polymerization and stabilization of the zwitterionic intermediate. Additionally, a preparative synthesis of 4-ferrocenyl-3-methylene-5-nitropentan-2-one was carried out and its synthetic transformations showed easy conversion to other useful building blocks.",
journal = "RSC Advances",
title = "Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction",
volume = "11",
number = "57",
pages = "36208-36214",
doi = "10.1039/D1RA07619A"
}
Stevanović, D. D., Bugarinović, J., Pešić, M., Todosijević, A., Bogdanović, G. A.,& Damljanović, I. S.. (2021). Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction. in RSC Advances, 11(57), 36208-36214.
https://doi.org/10.1039/D1RA07619A
Stevanović DD, Bugarinović J, Pešić M, Todosijević A, Bogdanović GA, Damljanović IS. Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction. in RSC Advances. 2021;11(57):36208-36214.
doi:10.1039/D1RA07619A .
Stevanović, Dragana D., Bugarinović, Jovana, Pešić, Marko, Todosijević, Anka, Bogdanović, Goran A., Damljanović, Ivan S., "Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction" in RSC Advances, 11, no. 57 (2021):36208-36214,
https://doi.org/10.1039/D1RA07619A . .
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Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction

Stevanović, Dragana D.; Bugarinović, Jovana; Pešić, Marko; Todosijević, Anka; Bogdanović, Goran A.; Damljanović, Ivan S.

(2021)

TY  - DATA
AU  - Stevanović, Dragana D.
AU  - Bugarinović, Jovana
AU  - Pešić, Marko
AU  - Todosijević, Anka
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10085
AB  - Electronic supplementary information (ESI) available: Detailed experimental procedures, spectral characterisation (including copies of 1H and 13C NMR spectra) of all new compounds, crystallographic data and CIF file. CCDC 2095955. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/D1RA07619A
T2  - RSC Advances
T1  - Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction
VL  - 11
IS  - 57
SP  - S1
EP  - S43
DO  - 10.1039/D1RA07619A
ER  - 
@misc{
author = "Stevanović, Dragana D. and Bugarinović, Jovana and Pešić, Marko and Todosijević, Anka and Bogdanović, Goran A. and Damljanović, Ivan S.",
year = "2021",
abstract = "Electronic supplementary information (ESI) available: Detailed experimental procedures, spectral characterisation (including copies of 1H and 13C NMR spectra) of all new compounds, crystallographic data and CIF file. CCDC 2095955. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/D1RA07619A",
journal = "RSC Advances",
title = "Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction",
volume = "11",
number = "57",
pages = "S1-S43",
doi = "10.1039/D1RA07619A"
}
Stevanović, D. D., Bugarinović, J., Pešić, M., Todosijević, A., Bogdanović, G. A.,& Damljanović, I. S.. (2021). Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction. in RSC Advances, 11(57), S1-S43.
https://doi.org/10.1039/D1RA07619A
Stevanović DD, Bugarinović J, Pešić M, Todosijević A, Bogdanović GA, Damljanović IS. Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction. in RSC Advances. 2021;11(57):S1-S43.
doi:10.1039/D1RA07619A .
Stevanović, Dragana D., Bugarinović, Jovana, Pešić, Marko, Todosijević, Anka, Bogdanović, Goran A., Damljanović, Ivan S., "Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction" in RSC Advances, 11, no. 57 (2021):S1-S43,
https://doi.org/10.1039/D1RA07619A . .
2

CCDC 2095955: Experimental Crystal Structure Determination

Stevanović, Dragana D.; Bugarinović, Jovana; Pešić, Marko; Todosijević, Anka; Bogdanović, Goran A.; Damljanović, Ivan S.

(2021)

TY  - DATA
AU  - Stevanović, Dragana D.
AU  - Bugarinović, Jovana
AU  - Pešić, Marko
AU  - Todosijević, Anka
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10086
AB  - ZAQGIL : 1,3-Diferrocenyl-2-methylene-4-nitrobutan-1-one Space Group: P 1 (2), Cell: a 5.89550(10)Å b 12.6957(3)Å c 15.6399(4)Å, α 66.206(2)° β 86.515(2)° γ 80.988(2)°
T2  - CCDC
T1  - CCDC 2095955: Experimental Crystal Structure Determination
DO  - 10.5517/ccdc.csd.cc28c0g4
ER  - 
@misc{
author = "Stevanović, Dragana D. and Bugarinović, Jovana and Pešić, Marko and Todosijević, Anka and Bogdanović, Goran A. and Damljanović, Ivan S.",
year = "2021",
abstract = "ZAQGIL : 1,3-Diferrocenyl-2-methylene-4-nitrobutan-1-one Space Group: P 1 (2), Cell: a 5.89550(10)Å b 12.6957(3)Å c 15.6399(4)Å, α 66.206(2)° β 86.515(2)° γ 80.988(2)°",
journal = "CCDC",
title = "CCDC 2095955: Experimental Crystal Structure Determination",
doi = "10.5517/ccdc.csd.cc28c0g4"
}
Stevanović, D. D., Bugarinović, J., Pešić, M., Todosijević, A., Bogdanović, G. A.,& Damljanović, I. S.. (2021). CCDC 2095955: Experimental Crystal Structure Determination. in CCDC.
https://doi.org/10.5517/ccdc.csd.cc28c0g4
Stevanović DD, Bugarinović J, Pešić M, Todosijević A, Bogdanović GA, Damljanović IS. CCDC 2095955: Experimental Crystal Structure Determination. in CCDC. 2021;.
doi:10.5517/ccdc.csd.cc28c0g4 .
Stevanović, Dragana D., Bugarinović, Jovana, Pešić, Marko, Todosijević, Anka, Bogdanović, Goran A., Damljanović, Ivan S., "CCDC 2095955: Experimental Crystal Structure Determination" in CCDC (2021),
https://doi.org/10.5517/ccdc.csd.cc28c0g4 . .

Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines

Pešić, Marko; Bugarinović, Jovana; Minić, Aleksandra; Bogdanović, Goran A.; Todosijević, Anka; Stevanović, Dragana D.; Damljanović, Ivan S.

(2020)

TY  - JOUR
AU  - Pešić, Marko
AU  - Bugarinović, Jovana
AU  - Minić, Aleksandra
AU  - Bogdanović, Goran A.
AU  - Todosijević, Anka
AU  - Stevanović, Dragana D.
AU  - Damljanović, Ivan S.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8892
AB  - The design, synthesis, spectral and electrochemical characterization of a series of novel pyrrolidine derivatives have been described. The synthesis was achieved by 1,3-dipolar cycloaddition of azomethine ylides and ferrocene-substituted chalcones, while detailed characterization of the compounds was performed by IR, NMR and elemental analyses, followed by X-ray diffraction experiment for one representative. The electrochemical properties of obtained ferrocene-containing heterocycles were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. DNA-binding capacity of all products was studied using CV and DPV, highlighting a derivative with five times better binding affinity than the others. DFT calculations and molecular docking studies were carried out to gain more exhaustive insight into the type of interactions of the distinguished compound and the nucleic acid.
T2  - Journal of The Electrochemical Society
T1  - Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines
VL  - 167
IS  - 2
SP  - 025502
DO  - 10.1149/1945-7111/ab68cc
ER  - 
@article{
author = "Pešić, Marko and Bugarinović, Jovana and Minić, Aleksandra and Bogdanović, Goran A. and Todosijević, Anka and Stevanović, Dragana D. and Damljanović, Ivan S.",
year = "2020",
abstract = "The design, synthesis, spectral and electrochemical characterization of a series of novel pyrrolidine derivatives have been described. The synthesis was achieved by 1,3-dipolar cycloaddition of azomethine ylides and ferrocene-substituted chalcones, while detailed characterization of the compounds was performed by IR, NMR and elemental analyses, followed by X-ray diffraction experiment for one representative. The electrochemical properties of obtained ferrocene-containing heterocycles were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. DNA-binding capacity of all products was studied using CV and DPV, highlighting a derivative with five times better binding affinity than the others. DFT calculations and molecular docking studies were carried out to gain more exhaustive insight into the type of interactions of the distinguished compound and the nucleic acid.",
journal = "Journal of The Electrochemical Society",
title = "Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines",
volume = "167",
number = "2",
pages = "025502",
doi = "10.1149/1945-7111/ab68cc"
}
Pešić, M., Bugarinović, J., Minić, A., Bogdanović, G. A., Todosijević, A., Stevanović, D. D.,& Damljanović, I. S.. (2020). Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines. in Journal of The Electrochemical Society, 167(2), 025502.
https://doi.org/10.1149/1945-7111/ab68cc
Pešić M, Bugarinović J, Minić A, Bogdanović GA, Todosijević A, Stevanović DD, Damljanović IS. Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines. in Journal of The Electrochemical Society. 2020;167(2):025502.
doi:10.1149/1945-7111/ab68cc .
Pešić, Marko, Bugarinović, Jovana, Minić, Aleksandra, Bogdanović, Goran A., Todosijević, Anka, Stevanović, Dragana D., Damljanović, Ivan S., "Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines" in Journal of The Electrochemical Society, 167, no. 2 (2020):025502,
https://doi.org/10.1149/1945-7111/ab68cc . .
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