Debromination of endo-(+)-3-Bromocamphor with Primary Amines

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

Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071

Supplementary material for: [https://doi.org/10.1016/j.ejmech.2013.03.071]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1370

Supplementary data for article: Marković, V.; Markovic, S.; Janicijevic, A.; Rodić, M.; Leovac, V. M.; Todorović, N.; Trifunović, S. S.; Joksović, M. D. Mechanistic Investigation and DFT Calculation of the New Reaction between S-Methylisothiosemicarbazide and Methyl Acetoacetate. Structural Chemistry 2013, 24 (6), 2127–2136. https://doi.org/10.1007/s11224-013-0223-3

Supplementary material for: [https://doi.org/10.1007/s11224-013-0223-3]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1455

Supplementary data for the article: Petrović, M. M.; Roschger, C.; Chaudary, S.; Zierer, A.; Mladenović, M.; Marković, V.; Trifunović, S.; Joksović, M. D. Low Cytotoxic Quinoline-4-Carboxylic Acids Derived from Vanillin Precursors as Potential Human Dihydroorotate Dehydrogenase Inhibitors. Bioorganic & Medicinal Chemistry Letters 2021, 46, 128194. https://doi.org/10.1016/j.bmcl.2021.128194.

Supplementary material for: [https://doi.org/10.1016/j.bmcl.2021.128194]Related to published version: [https://cherry.chem.bg.ac.rs/handle/123456789/4550

Supplementary data for article: Marković, V.; Erić, S.; Stanojković, T.; Gligorijević, N.; Aranđelović, S.; Todorović, N.; Trifunović, S. S.; Manojlović, N.; Jelic, R.; Joksović, M. D. Antiproliferative Activity and QSAR Studies of a Series of New 4-Aminomethylidene Derivatives of Some Pyrazol-5-Ones. Bioorganic and Medicinal Chemistry Letters 2011, 21 (15), 4416–4421. https://doi.org/10.1016/j.bmcl.2011.06.025

Supplementary material for: [https://doi.org/10.1016/j.bmcl.2011.06.025]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1175

Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071

Supplementary material for: [https://doi.org/10.1016/j.ejmech.2013.03.071]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1370

Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697. https://doi.org/10.1039/c8md00316e

Supplementary material for: [https://pubs.rsc.org/en/content/articlelanding/2018/MD/C8MD00316E#!divAbstract]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2089]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/2892

Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920

Supporting Information: [https://doi.org/10.1111/cbdd.12920]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2482]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/3221

Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920

Supporting Information: [https://doi.org/10.1111/cbdd.12920]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2482]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/3221

Supplementary data for article: Marković, V.; Markovic, S.; Janicijevic, A.; Rodić, M.; Leovac, V. M.; Todorović, N.; Trifunović, S. S.; Joksović, M. D. Mechanistic Investigation and DFT Calculation of the New Reaction between S-Methylisothiosemicarbazide and Methyl Acetoacetate. Structural Chemistry 2013, 24 (6), 2127–2136. https://doi.org/10.1007/s11224-013-0223-3

Supplementary material for: [https://doi.org/10.1007/s11224-013-0223-3]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1455