TY  - JOUR
AU  - Marković, Violeta
AU  - Marković, Svetlana
AU  - Janićijević, Ana
AU  - Rodić, Marko
AU  - Leovac, Vukadin M.
AU  - Todorović, Nina
AU  - Trifunović, Snežana S.
AU  - Joksović, Milan D.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1455
AB  - A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
VL  - 24
IS  - 6
SP  - 2127
EP  - 2136
DO  - 10.1007/s11224-013-0223-3
ER  - 

@article{
author = "Marković, Violeta and Marković, Svetlana and Janićijević, Ana and Rodić, Marko and Leovac, Vukadin M. and Todorović, Nina and Trifunović, Snežana S. and Joksović, Milan D.",
year = "2013",
abstract = "A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate",
volume = "24",
number = "6",
pages = "2127-2136",
doi = "10.1007/s11224-013-0223-3"
}

Marković, V., Marković, S., Janićijević, A., Rodić, M., Leovac, V. M., Todorović, N., Trifunović, S. S.,& Joksović, M. D.. (2013). Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry
Springer/Plenum Publishers, New York., 24(6), 2127-2136.
https://doi.org/10.1007/s11224-013-0223-3

Marković V, Marković S, Janićijević A, Rodić M, Leovac VM, Todorović N, Trifunović SS, Joksović MD. Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry. 2013;24(6):2127-2136.
doi:10.1007/s11224-013-0223-3 .

Marković, Violeta, Marković, Svetlana, Janićijević, Ana, Rodić, Marko, Leovac, Vukadin M., Todorović, Nina, Trifunović, Snežana S., Joksović, Milan D., "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate" in Structural Chemistry, 24, no. 6 (2013):2127-2136,
https://doi.org/10.1007/s11224-013-0223-3 . .

TY  - JOUR
AU  - Marković, Svetlana
AU  - Marković, Violeta
AU  - Joksović, Milan D.
AU  - Todorović, Nina
AU  - Joksović, Ljubinka
AU  - Divjaković, Vladimir
AU  - Trifunović, Snežana S.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1385
AB  - Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.
PB  - Soc Brasileira Quimica, Sao Paulo
T2  - Journal of the Brazilian Chemical Society
T1  - Debromination of endo-(+)-3-Bromocamphor with Primary Amines
VL  - 24
IS  - 7
SP  - 1099
DO  - 10.5935/0103-5053.20130144
ER  - 

@article{
author = "Marković, Svetlana and Marković, Violeta and Joksović, Milan D. and Todorović, Nina and Joksović, Ljubinka and Divjaković, Vladimir and Trifunović, Snežana S.",
year = "2013",
abstract = "Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.",
publisher = "Soc Brasileira Quimica, Sao Paulo",
journal = "Journal of the Brazilian Chemical Society",
title = "Debromination of endo-(+)-3-Bromocamphor with Primary Amines",
volume = "24",
number = "7",
pages = "1099",
doi = "10.5935/0103-5053.20130144"
}

Marković, S., Marković, V., Joksović, M. D., Todorović, N., Joksović, L., Divjaković, V.,& Trifunović, S. S.. (2013). Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society
Soc Brasileira Quimica, Sao Paulo., 24(7), 1099.
https://doi.org/10.5935/0103-5053.20130144

Marković S, Marković V, Joksović MD, Todorović N, Joksović L, Divjaković V, Trifunović SS. Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society. 2013;24(7):1099.
doi:10.5935/0103-5053.20130144 .

Marković, Svetlana, Marković, Violeta, Joksović, Milan D., Todorović, Nina, Joksović, Ljubinka, Divjaković, Vladimir, Trifunović, Snežana S., "Debromination of endo-(+)-3-Bromocamphor with Primary Amines" in Journal of the Brazilian Chemical Society, 24, no. 7 (2013):1099,
https://doi.org/10.5935/0103-5053.20130144 . .