TY  - JOUR
AU  - Jevtić, Ivana I.
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Todorović, Nina
AU  - Ivanović, Milovan
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3248
AB  - The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl
VL  - 49
IS  - 14
SP  - 3126
EP  - 3136
DO  - 10.1055/s-0036-1588985
ER  - 

@article{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Todorović, Nina and Ivanović, Milovan",
year = "2017",
abstract = "The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl",
volume = "49",
number = "14",
pages = "3126-3136",
doi = "10.1055/s-0036-1588985"
}

Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R., Todorović, N.,& Ivanović, M.. (2017). Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. in Synthesis
Georg Thieme Verlag Kg, Stuttgart., 49(14), 3126-3136.
https://doi.org/10.1055/s-0036-1588985

Jevtić II, Došen-Mićović L, Ivanović ER, Todorović N, Ivanović M. Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. in Synthesis. 2017;49(14):3126-3136.
doi:10.1055/s-0036-1588985 .

Jevtić, Ivana I., Došen-Mićović, Ljiljana, Ivanović, Evica R., Todorović, Nina, Ivanović, Milovan, "Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl" in Synthesis, 49, no. 14 (2017):3126-3136,
https://doi.org/10.1055/s-0036-1588985 . .

TY  - DATA
AU  - Jevtić, Ivana I.
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Todorović, Nina
AU  - Ivanović, Milovan
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3249
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3249
ER  - 

@misc{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Todorović, Nina and Ivanović, Milovan",
year = "2017",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3249"
}

Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R., Todorović, N.,& Ivanović, M.. (2017). Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985. in Synthesis
Georg Thieme Verlag Kg, Stuttgart..
https://hdl.handle.net/21.15107/rcub_cherry_3249

Jevtić II, Došen-Mićović L, Ivanović ER, Todorović N, Ivanović M. Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985. in Synthesis. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3249 .

Jevtić, Ivana I., Došen-Mićović, Ljiljana, Ivanović, Evica R., Todorović, Nina, Ivanović, Milovan, "Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985" in Synthesis (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3249 .