Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines
Само за регистроване кориснике
2018
Аутори
Jovanović, Jovana P.Novaković, Slađana B.
Bogdanović, Goran A.
Minić, Aleksandra
Pejović, Anka
Katanić, Jelena
Mihailović, Vladimir B.
Nastasijević, Branislav J.
Stevanović, Dragana D.
Damljanović, Ivan S.
Чланак у часопису (Објављена верзија)
,
© 2018 Elsevier B.V.
Метаподаци
Приказ свих података о документуАпстракт
AlCl3-Catalyzed {[}3 + 2] dipolar cycloaddition of the N,N'-cyclic azomethine imines to the acryloylferrocene enabling access to the series of 5-substituted 6-ferrocenoyl tetrahydropyrazolo {[}1,2-a]pyrazol-1(5H)-ones. This facile methodology shows high substituent tolerance. Furthermore, easy chromatographic separations afford isolation of the pure diastereoisomers. Optimized reaction conditions, spectroscopic and electrochemical characteristics of the reaction products are provided. The X-ray structural analyses of three cycloadducts were done and obtained results were compared with properties of reported N,N'-bicyclic systems those displayed conformational similarity. Antibacterial activities of all products against two Gram-positive and two Gram-negative bacterial strains were evaluated by the experimental methods. (c) 2018 Elsevier B.V. All rights reserved.
Кључне речи:
1,3-Dipolar cycloaddition / antibacterial activity / acryloylferrocene / N,N`-cyclic azomethine imines / tetrahydropyrazolopyrazolonesИзвор:
Journal of Organometallic Chemistry, 2018, 860, 85-97Финансирање / пројекти:
- Симултана биоремедијација и соилификација деградираних простора, за очување природних ресурса биолошки активних супстанци и развој и производњу биоматеријала и дијететских производа (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-43004)
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
- Нове електрохемијске и хемијске методе у синтези органских једињења од интереса за медицину и хемију материјала (RS-MESTD-Basic Research (BR or ON)-172034)
DOI: 10.1016/j.jorganchem.2018.02.016
ISSN: 0022-328X; 1872-8561
WoS: 000427517000009
Scopus: 2-s2.0-85042468442
Колекције
Институција/група
VinčaTY - JOUR AU - Jovanović, Jovana P. AU - Novaković, Slađana B. AU - Bogdanović, Goran A. AU - Minić, Aleksandra AU - Pejović, Anka AU - Katanić, Jelena AU - Mihailović, Vladimir B. AU - Nastasijević, Branislav J. AU - Stevanović, Dragana D. AU - Damljanović, Ivan S. PY - 2018 UR - https://vinar.vin.bg.ac.rs/handle/123456789/7635 AB - AlCl3-Catalyzed {[}3 + 2] dipolar cycloaddition of the N,N'-cyclic azomethine imines to the acryloylferrocene enabling access to the series of 5-substituted 6-ferrocenoyl tetrahydropyrazolo {[}1,2-a]pyrazol-1(5H)-ones. This facile methodology shows high substituent tolerance. Furthermore, easy chromatographic separations afford isolation of the pure diastereoisomers. Optimized reaction conditions, spectroscopic and electrochemical characteristics of the reaction products are provided. The X-ray structural analyses of three cycloadducts were done and obtained results were compared with properties of reported N,N'-bicyclic systems those displayed conformational similarity. Antibacterial activities of all products against two Gram-positive and two Gram-negative bacterial strains were evaluated by the experimental methods. (c) 2018 Elsevier B.V. All rights reserved. T2 - Journal of Organometallic Chemistry T1 - Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines VL - 860 SP - 85 EP - 97 DO - 10.1016/j.jorganchem.2018.02.016 ER -
@article{ author = "Jovanović, Jovana P. and Novaković, Slađana B. and Bogdanović, Goran A. and Minić, Aleksandra and Pejović, Anka and Katanić, Jelena and Mihailović, Vladimir B. and Nastasijević, Branislav J. and Stevanović, Dragana D. and Damljanović, Ivan S.", year = "2018", abstract = "AlCl3-Catalyzed {[}3 + 2] dipolar cycloaddition of the N,N'-cyclic azomethine imines to the acryloylferrocene enabling access to the series of 5-substituted 6-ferrocenoyl tetrahydropyrazolo {[}1,2-a]pyrazol-1(5H)-ones. This facile methodology shows high substituent tolerance. Furthermore, easy chromatographic separations afford isolation of the pure diastereoisomers. Optimized reaction conditions, spectroscopic and electrochemical characteristics of the reaction products are provided. The X-ray structural analyses of three cycloadducts were done and obtained results were compared with properties of reported N,N'-bicyclic systems those displayed conformational similarity. Antibacterial activities of all products against two Gram-positive and two Gram-negative bacterial strains were evaluated by the experimental methods. (c) 2018 Elsevier B.V. All rights reserved.", journal = "Journal of Organometallic Chemistry", title = "Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines", volume = "860", pages = "85-97", doi = "10.1016/j.jorganchem.2018.02.016" }
Jovanović, J. P., Novaković, S. B., Bogdanović, G. A., Minić, A., Pejović, A., Katanić, J., Mihailović, V. B., Nastasijević, B. J., Stevanović, D. D.,& Damljanović, I. S.. (2018). Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines. in Journal of Organometallic Chemistry, 860, 85-97. https://doi.org/10.1016/j.jorganchem.2018.02.016
Jovanović JP, Novaković SB, Bogdanović GA, Minić A, Pejović A, Katanić J, Mihailović VB, Nastasijević BJ, Stevanović DD, Damljanović IS. Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines. in Journal of Organometallic Chemistry. 2018;860:85-97. doi:10.1016/j.jorganchem.2018.02.016 .
Jovanović, Jovana P., Novaković, Slađana B., Bogdanović, Goran A., Minić, Aleksandra, Pejović, Anka, Katanić, Jelena, Mihailović, Vladimir B., Nastasijević, Branislav J., Stevanović, Dragana D., Damljanović, Ivan S., "Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines" in Journal of Organometallic Chemistry, 860 (2018):85-97, https://doi.org/10.1016/j.jorganchem.2018.02.016 . .