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Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines

Authorized Users Only
2018
Authors
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.
Article (Published version)
,
© 2018 Elsevier B.V.
Metadata
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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.
Keywords:
1,3-Dipolar cycloaddition / antibacterial activity / acryloylferrocene / N,N`-cyclic azomethine imines / tetrahydropyrazolopyrazolones
Source:
Journal of Organometallic Chemistry, 2018, 860, 85-97
Funding / projects:
  • Simultaneous Bioremediation and Soilification of Degraded Areas to Preserve Natural Resources of Biologically Active Substances, and Development and Production of Biomaterials and Dietetic Products (RS-43004)
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-172034)

DOI: 10.1016/j.jorganchem.2018.02.016

ISSN: 0022-328X; 1872-8561

WoS: 000427517000009

Scopus: 2-s2.0-85042468442
[ Google Scholar ]
8
7
URI
https://vinar.vin.bg.ac.rs/handle/123456789/7635
Collections
  • Radovi istraživača
Institution/Community
Vinča
TY  - 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 . .

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