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Synthesis of New Functionally Substituted 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-Catalyzed [6π + 2π]-Cycloaddition of N-Carbocholesteroxyazepine to Alkynes
Publication type: Journal Article
Publication date: 2021-05-14
PubMed ID:
34069183
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
Catalytic [6π + 2π]-cycloaddition of N-carbocholesteroxyazepine with functionally substituted terminal alkynes and 1,4-butynediol was performed for the first time under the action of the Co(acac)2(dppe)/Zn/ZnI2 three-component catalytic system. The reaction gave previously undescribed but promising 9-azabicyclo[4.2.1]nona-2,4,7-trienes (in 79–95% yields), covalently bound to a natural metabolite, cholesterol. The structure of the synthesized azabicycles was confirmed by analysis of one- and two-dimensional (1H, 13C, DEPT 13C, COSY, NOESY, HSQC, HMBC) NMR spectra.
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Kadikova G. N., D'yakonov V. A., Dzhemilev U. M. Synthesis of New Functionally Substituted 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-Catalyzed [6π + 2π]-Cycloaddition of N-Carbocholesteroxyazepine to Alkynes // Molecules. 2021. Vol. 26. No. 10. p. 2932.
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Kadikova G. N., D'yakonov V. A., Dzhemilev U. M. Synthesis of New Functionally Substituted 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-Catalyzed [6π + 2π]-Cycloaddition of N-Carbocholesteroxyazepine to Alkynes // Molecules. 2021. Vol. 26. No. 10. p. 2932.
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TY - JOUR
DO - 10.3390/molecules26102932
UR - https://doi.org/10.3390/molecules26102932
TI - Synthesis of New Functionally Substituted 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-Catalyzed [6π + 2π]-Cycloaddition of N-Carbocholesteroxyazepine to Alkynes
T2 - Molecules
AU - Kadikova, Gulnara N.
AU - D'yakonov, Vladimir A
AU - Dzhemilev, Usein M.
PY - 2021
DA - 2021/05/14
PB - MDPI
SP - 2932
IS - 10
VL - 26
PMID - 34069183
SN - 1420-3049
ER -
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@article{2021_Kadikova,
author = {Gulnara N. Kadikova and Vladimir A D'yakonov and Usein M. Dzhemilev},
title = {Synthesis of New Functionally Substituted 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-Catalyzed [6π + 2π]-Cycloaddition of N-Carbocholesteroxyazepine to Alkynes},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {MDPI},
month = {may},
url = {https://doi.org/10.3390/molecules26102932},
number = {10},
pages = {2932},
doi = {10.3390/molecules26102932}
}
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MLA
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Kadikova, Gulnara N., et al. “Synthesis of New Functionally Substituted 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-Catalyzed [6π + 2π]-Cycloaddition of N-Carbocholesteroxyazepine to Alkynes.” Molecules, vol. 26, no. 10, May. 2021, p. 2932. https://doi.org/10.3390/molecules26102932.