TY  - JOUR
AU  - Minić, Aleksandra
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Bugarinović, Jovana P.
AU  - Pešić, Marko S.
AU  - Todosijević, Anka
AU  - Ilić-Komatina, Danijela
AU  - Damljanović, Ivan S.
AU  - Stevanović, Dragana D.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8808
AB  - The stereochemical phenomenon that arises from hindered rotation around bonds in nonplanar molecules is termed the atropoisomerism. During our previous work we noted the presence of this kind of isomerism in 1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones obtained from ortho-substituted 3-(arylamino)-1-ferrocenylpropan-1-ols. Inspired by an interesting biological/medical features of six-membered cyclic ureas and characteristic of “atropoisomers - things that rotate”, herein we present an easy performable synthesis and full characterisation of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. In addition, we successfully determined the crystal structure of two atropoisomers for the same compound. Molecular structural properties and intermolecular interactions of these two structures have been compared and analyzed in detail. Interesting, it has been found that these two isomers although quite similar in conformation and geometrical parameters, form very different crystal packing. © 2019 Elsevier Ltd
T2  - Polyhedron
T1  - Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas
VL  - 177
SP  - 114316
DO  - 10.1016/j.poly.2019.114316
ER  - 

@article{
author = "Minić, Aleksandra and Novaković, Slađana B. and Bogdanović, Goran A. and Bugarinović, Jovana P. and Pešić, Marko S. and Todosijević, Anka and Ilić-Komatina, Danijela and Damljanović, Ivan S. and Stevanović, Dragana D.",
year = "2020",
abstract = "The stereochemical phenomenon that arises from hindered rotation around bonds in nonplanar molecules is termed the atropoisomerism. During our previous work we noted the presence of this kind of isomerism in 1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones obtained from ortho-substituted 3-(arylamino)-1-ferrocenylpropan-1-ols. Inspired by an interesting biological/medical features of six-membered cyclic ureas and characteristic of “atropoisomers - things that rotate”, herein we present an easy performable synthesis and full characterisation of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. In addition, we successfully determined the crystal structure of two atropoisomers for the same compound. Molecular structural properties and intermolecular interactions of these two structures have been compared and analyzed in detail. Interesting, it has been found that these two isomers although quite similar in conformation and geometrical parameters, form very different crystal packing. © 2019 Elsevier Ltd",
journal = "Polyhedron",
title = "Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas",
volume = "177",
pages = "114316",
doi = "10.1016/j.poly.2019.114316"
}

Minić, A., Novaković, S. B., Bogdanović, G. A., Bugarinović, J. P., Pešić, M. S., Todosijević, A., Ilić-Komatina, D., Damljanović, I. S.,& Stevanović, D. D.. (2020). Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. in Polyhedron, 177, 114316.
https://doi.org/10.1016/j.poly.2019.114316

Minić A, Novaković SB, Bogdanović GA, Bugarinović JP, Pešić MS, Todosijević A, Ilić-Komatina D, Damljanović IS, Stevanović DD. Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. in Polyhedron. 2020;177:114316.
doi:10.1016/j.poly.2019.114316 .

Minić, Aleksandra, Novaković, Slađana B., Bogdanović, Goran A., Bugarinović, Jovana P., Pešić, Marko S., Todosijević, Anka, Ilić-Komatina, Danijela, Damljanović, Ivan S., Stevanović, Dragana D., "Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas" in Polyhedron, 177 (2020):114316,
https://doi.org/10.1016/j.poly.2019.114316 . .

TY  - JOUR
AU  - Minić, Aleksandra
AU  - Pešić, Marko S
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Todosijević, Anka
AU  - Ilić-Komatina, Danijela
AU  - Stevanović, Dragana D.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9119
AB  - Herein, we report an easy performable method for the synthesis of ferrocene-containing tetrahydropyrimidin-2(1H)-ones starting from the corresponding 3-arylamino-1-ferrocenylpropan-1-ols and sodium cyanate (NaOCN) in the presence of glacial acetic acid. The protocol is included an intramolecular cyclization of an in situ generated 1,3-hydroxyurea. The scope of the reaction towards eleven ferrocene-containing 1,3-amino alcohols has been explored and the targeted 1-aryl-4-ferrocenyltetrahidropyrimidin-2(1H)-ones were obtained in good to high yields (up to 93%). All products have been isolated in high purity >95%. In addition, we have provided a detailed structural characterization of the new compounds, which has been performed by IR and NMR spectroscopy. The single-crystal X-ray diffraction analysis was successfully performed on three representative examples, as well as elemental analysis. Moreover, molecular structure properties and intermolecular interactions of these three structures have been compared and analyzed in detail. Electrochemical properties of products were investigated by cyclic voltammetry. This investigation revealed the quasi-reversible one-electron redox process.
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones
VL  - 923
SP  - 121422
DO  - 10.1016/j.jorganchem.2020.121422
ER  - 

@article{
author = "Minić, Aleksandra and Pešić, Marko S and Novaković, Slađana B. and Bogdanović, Goran A. and Todosijević, Anka and Ilić-Komatina, Danijela and Stevanović, Dragana D.",
year = "2020",
abstract = "Herein, we report an easy performable method for the synthesis of ferrocene-containing tetrahydropyrimidin-2(1H)-ones starting from the corresponding 3-arylamino-1-ferrocenylpropan-1-ols and sodium cyanate (NaOCN) in the presence of glacial acetic acid. The protocol is included an intramolecular cyclization of an in situ generated 1,3-hydroxyurea. The scope of the reaction towards eleven ferrocene-containing 1,3-amino alcohols has been explored and the targeted 1-aryl-4-ferrocenyltetrahidropyrimidin-2(1H)-ones were obtained in good to high yields (up to 93%). All products have been isolated in high purity >95%. In addition, we have provided a detailed structural characterization of the new compounds, which has been performed by IR and NMR spectroscopy. The single-crystal X-ray diffraction analysis was successfully performed on three representative examples, as well as elemental analysis. Moreover, molecular structure properties and intermolecular interactions of these three structures have been compared and analyzed in detail. Electrochemical properties of products were investigated by cyclic voltammetry. This investigation revealed the quasi-reversible one-electron redox process.",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones",
volume = "923",
pages = "121422",
doi = "10.1016/j.jorganchem.2020.121422"
}

Minić, A., Pešić, M. S., Novaković, S. B., Bogdanović, G. A., Todosijević, A., Ilić-Komatina, D.,& Stevanović, D. D.. (2020). Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones. in Journal of Organometallic Chemistry, 923, 121422.
https://doi.org/10.1016/j.jorganchem.2020.121422

Minić A, Pešić MS, Novaković SB, Bogdanović GA, Todosijević A, Ilić-Komatina D, Stevanović DD. Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones. in Journal of Organometallic Chemistry. 2020;923:121422.
doi:10.1016/j.jorganchem.2020.121422 .

Minić, Aleksandra, Pešić, Marko S, Novaković, Slađana B., Bogdanović, Goran A., Todosijević, Anka, Ilić-Komatina, Danijela, Stevanović, Dragana D., "Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones" in Journal of Organometallic Chemistry, 923 (2020):121422,
https://doi.org/10.1016/j.jorganchem.2020.121422 . .

TY  - JOUR
AU  - Bugarinović, Jovana P.
AU  - Pešić, Marko S.
AU  - Minić, Aleksandra
AU  - Katanić, Jelena
AU  - Ilić-Komatina, Danijela
AU  - Pejović, Anka
AU  - Mihailović, Vladimir B.
AU  - Stevanović, Dragana D.
AU  - Nastasijević, Branislav J.
AU  - Damljanović, Ivan S.
PY  - 2018
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0162013418302472
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7890
AB  - A series of ferrocenes which contain dinitrogen-fused pyrazolidinone ring were synthesized from acryloylferrocene (4) and N,N′‑cyclic azomethine imines (3). Novel 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones were obtained as mixtures of two diastereoisomers (trans and cis) which were separated and isolated as pure substances. Ortho-substituted N,N′‑cyclic azomethine imines 5-oxo-2-(2,4,6-trimethylbenzylidene)pyrazolidin-2-ium-1-ide (3e) and 2-(2-methoxybenzylidene)-5-oxopyrazolidin-2-ium-1-ide (3f) reacted stereoselectively affording only trans-6-ferrocenoyl-5-mesityltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5e) and 6-ferrocenoyl-5-(2-methoxyphenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5f). Ferrocenyl derivatives were screened for in vitro antioxidant and antifungal activities and excellent DPPH and ABTS radicals scavenging activity was observed with majority of tested 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones. Several tested compounds showed selective scavenging properties neutralizing ABTS•+ radical cations in contrast to inactivity toward DPPH[rad] radicals. Trans-5-aryl-6-ferrocenoyltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-ones 5b, 5c, 5d, 5j as well as cis-6-ferrocenoyl-5-(p-tolyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6d) displayed fungal growth inhibition at low concentration against C. albicans and/or A. brasiliensis. Molecular docking studies revealed that the cis-6-ferrocenoyl-5-(4-nitrophenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6l) and cis-6-ferrocenoyl-5-(naphthalen-2-yl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6n) have potential to become lead molecules in drug discovery process. © 2018 Elsevier Inc.
T2  - Journal of Inorganic Biochemistry
T1  - Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity
VL  - 189
SP  - 134
EP  - 142
DO  - 10.1016/j.jinorgbio.2018.09.015
ER  - 

@article{
author = "Bugarinović, Jovana P. and Pešić, Marko S. and Minić, Aleksandra and Katanić, Jelena and Ilić-Komatina, Danijela and Pejović, Anka and Mihailović, Vladimir B. and Stevanović, Dragana D. and Nastasijević, Branislav J. and Damljanović, Ivan S.",
year = "2018",
abstract = "A series of ferrocenes which contain dinitrogen-fused pyrazolidinone ring were synthesized from acryloylferrocene (4) and N,N′‑cyclic azomethine imines (3). Novel 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones were obtained as mixtures of two diastereoisomers (trans and cis) which were separated and isolated as pure substances. Ortho-substituted N,N′‑cyclic azomethine imines 5-oxo-2-(2,4,6-trimethylbenzylidene)pyrazolidin-2-ium-1-ide (3e) and 2-(2-methoxybenzylidene)-5-oxopyrazolidin-2-ium-1-ide (3f) reacted stereoselectively affording only trans-6-ferrocenoyl-5-mesityltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5e) and 6-ferrocenoyl-5-(2-methoxyphenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5f). Ferrocenyl derivatives were screened for in vitro antioxidant and antifungal activities and excellent DPPH and ABTS radicals scavenging activity was observed with majority of tested 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones. Several tested compounds showed selective scavenging properties neutralizing ABTS•+ radical cations in contrast to inactivity toward DPPH[rad] radicals. Trans-5-aryl-6-ferrocenoyltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-ones 5b, 5c, 5d, 5j as well as cis-6-ferrocenoyl-5-(p-tolyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6d) displayed fungal growth inhibition at low concentration against C. albicans and/or A. brasiliensis. Molecular docking studies revealed that the cis-6-ferrocenoyl-5-(4-nitrophenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6l) and cis-6-ferrocenoyl-5-(naphthalen-2-yl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6n) have potential to become lead molecules in drug discovery process. © 2018 Elsevier Inc.",
journal = "Journal of Inorganic Biochemistry",
title = "Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity",
volume = "189",
pages = "134-142",
doi = "10.1016/j.jinorgbio.2018.09.015"
}

Bugarinović, J. P., Pešić, M. S., Minić, A., Katanić, J., Ilić-Komatina, D., Pejović, A., Mihailović, V. B., Stevanović, D. D., Nastasijević, B. J.,& Damljanović, I. S.. (2018). Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity. in Journal of Inorganic Biochemistry, 189, 134-142.
https://doi.org/10.1016/j.jinorgbio.2018.09.015

Bugarinović JP, Pešić MS, Minić A, Katanić J, Ilić-Komatina D, Pejović A, Mihailović VB, Stevanović DD, Nastasijević BJ, Damljanović IS. Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity. in Journal of Inorganic Biochemistry. 2018;189:134-142.
doi:10.1016/j.jinorgbio.2018.09.015 .

Bugarinović, Jovana P., Pešić, Marko S., Minić, Aleksandra, Katanić, Jelena, Ilić-Komatina, Danijela, Pejović, Anka, Mihailović, Vladimir B., Stevanović, Dragana D., Nastasijević, Branislav J., Damljanović, Ivan S., "Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity" in Journal of Inorganic Biochemistry, 189 (2018):134-142,
https://doi.org/10.1016/j.jinorgbio.2018.09.015 . .

TY  - JOUR
AU  - Pejović, Anka
AU  - Minić, Aleksandra
AU  - Jovanović, Jovana P.
AU  - Pešić, Marko S.
AU  - Ilić-Komatina, Danijela
AU  - Damljanović, Ivan S.
AU  - Stevanović, Dragana D.
AU  - Mihailović, Vladimir B.
AU  - Katanić, Jelena
AU  - Bogdanović, Goran A.
PY  - 2018
UR  - http://linkinghub.elsevier.com/retrieve/pii/S0022328X18303796
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7701
AB  - Synthesis of twenty novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones has been achieved in good to excellent yields by the Knoevenagel condensation of 2-ferrocenyl-1,3-thiazolidin-4-ones with aromatic aldehydes. The reaction was performed by refluxing the mixture of reactants and potassium tert-butoxide in dioxane overnight. All new compounds were characterized by the IR and NMR spectral data, and their electrochemical properties were investigated using the cyclic voltammetry. The X-ray crystal structure of one of the representative thiazolidin-4(1H)-ones is also presented. All obtained products were evaluated for their in vitro antioxidant, antibacterial and antifungal activity.
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones
VL  - 869
SP  - 1
EP  - 10
DO  - 10.1016/j.jorganchem.2018.05.014
ER  - 

@article{
author = "Pejović, Anka and Minić, Aleksandra and Jovanović, Jovana P. and Pešić, Marko S. and Ilić-Komatina, Danijela and Damljanović, Ivan S. and Stevanović, Dragana D. and Mihailović, Vladimir B. and Katanić, Jelena and Bogdanović, Goran A.",
year = "2018",
abstract = "Synthesis of twenty novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones has been achieved in good to excellent yields by the Knoevenagel condensation of 2-ferrocenyl-1,3-thiazolidin-4-ones with aromatic aldehydes. The reaction was performed by refluxing the mixture of reactants and potassium tert-butoxide in dioxane overnight. All new compounds were characterized by the IR and NMR spectral data, and their electrochemical properties were investigated using the cyclic voltammetry. The X-ray crystal structure of one of the representative thiazolidin-4(1H)-ones is also presented. All obtained products were evaluated for their in vitro antioxidant, antibacterial and antifungal activity.",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones",
volume = "869",
pages = "1-10",
doi = "10.1016/j.jorganchem.2018.05.014"
}

Pejović, A., Minić, A., Jovanović, J. P., Pešić, M. S., Ilić-Komatina, D., Damljanović, I. S., Stevanović, D. D., Mihailović, V. B., Katanić, J.,& Bogdanović, G. A.. (2018). Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones. in Journal of Organometallic Chemistry, 869, 1-10.
https://doi.org/10.1016/j.jorganchem.2018.05.014

Pejović A, Minić A, Jovanović JP, Pešić MS, Ilić-Komatina D, Damljanović IS, Stevanović DD, Mihailović VB, Katanić J, Bogdanović GA. Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones. in Journal of Organometallic Chemistry. 2018;869:1-10.
doi:10.1016/j.jorganchem.2018.05.014 .

Pejović, Anka, Minić, Aleksandra, Jovanović, Jovana P., Pešić, Marko S., Ilić-Komatina, Danijela, Damljanović, Ivan S., Stevanović, Dragana D., Mihailović, Vladimir B., Katanić, Jelena, Bogdanović, Goran A., "Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones" in Journal of Organometallic Chemistry, 869 (2018):1-10,
https://doi.org/10.1016/j.jorganchem.2018.05.014 . .

TY  - JOUR
AU  - Minić, Aleksandra
AU  - Bugarinović, Jovana P.
AU  - Pejović, Anka
AU  - Ilić-Komatina, Danijela
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
AU  - Stevanović, Dragana D.
PY  - 2018
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0040403918310189
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7845
AB  - A simple one-pot synthesis of new ferrocene-containing 1,3-thiazinan-2-imines from 3-arylamino-1-ferrocenylpropan-1-ols and phenyl isothiocyanate has been developed. The key intermediate β-hydroxy thioureas were generated in situ using ultrasound irradiation and subsequent cyclization was achieved by the addition of acetic acid. The scope of the reaction towards various 3-arylamino-1-ferrocenylpropan-1-ols has been explored and the corresponding 3-aryl-6-ferrocenyl-N-phenyl-1,3-thiazinan-2-imines were obtained in moderate to high yields (52–90%).
T2  - Tetrahedron Letters
T1  - Synthesis of novel ferrocene-containing 1,3-thiazinan-2-imines: One-pot reaction promoted by ultrasound irradiation
VL  - 59
IS  - 38
SP  - 3499
EP  - 3502
DO  - 10.1016/j.tetlet.2018.08.029
ER  - 

@article{
author = "Minić, Aleksandra and Bugarinović, Jovana P. and Pejović, Anka and Ilić-Komatina, Danijela and Bogdanović, Goran A. and Damljanović, Ivan S. and Stevanović, Dragana D.",
year = "2018",
abstract = "A simple one-pot synthesis of new ferrocene-containing 1,3-thiazinan-2-imines from 3-arylamino-1-ferrocenylpropan-1-ols and phenyl isothiocyanate has been developed. The key intermediate β-hydroxy thioureas were generated in situ using ultrasound irradiation and subsequent cyclization was achieved by the addition of acetic acid. The scope of the reaction towards various 3-arylamino-1-ferrocenylpropan-1-ols has been explored and the corresponding 3-aryl-6-ferrocenyl-N-phenyl-1,3-thiazinan-2-imines were obtained in moderate to high yields (52–90%).",
journal = "Tetrahedron Letters",
title = "Synthesis of novel ferrocene-containing 1,3-thiazinan-2-imines: One-pot reaction promoted by ultrasound irradiation",
volume = "59",
number = "38",
pages = "3499-3502",
doi = "10.1016/j.tetlet.2018.08.029"
}

Minić, A., Bugarinović, J. P., Pejović, A., Ilić-Komatina, D., Bogdanović, G. A., Damljanović, I. S.,& Stevanović, D. D.. (2018). Synthesis of novel ferrocene-containing 1,3-thiazinan-2-imines: One-pot reaction promoted by ultrasound irradiation. in Tetrahedron Letters, 59(38), 3499-3502.
https://doi.org/10.1016/j.tetlet.2018.08.029

Minić A, Bugarinović JP, Pejović A, Ilić-Komatina D, Bogdanović GA, Damljanović IS, Stevanović DD. Synthesis of novel ferrocene-containing 1,3-thiazinan-2-imines: One-pot reaction promoted by ultrasound irradiation. in Tetrahedron Letters. 2018;59(38):3499-3502.
doi:10.1016/j.tetlet.2018.08.029 .

Minić, Aleksandra, Bugarinović, Jovana P., Pejović, Anka, Ilić-Komatina, Danijela, Bogdanović, Goran A., Damljanović, Ivan S., Stevanović, Dragana D., "Synthesis of novel ferrocene-containing 1,3-thiazinan-2-imines: One-pot reaction promoted by ultrasound irradiation" in Tetrahedron Letters, 59, no. 38 (2018):3499-3502,
https://doi.org/10.1016/j.tetlet.2018.08.029 . .