Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone

[Image: see text] The [6π + 2π] cycloaddition of 2-tropylcyclohexanone to allenes and alkynes was accomplished for the first time using the three-component catalytic system Co(acac)(2)(dppe)/Zn/ZnI(2), thus giving previously unknown functionally substituted bicyclo[4.2.1]nona-2,4-dienes and bicyclo[...

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Autores principales: Kadikova, Gulnara N., Dzhemileva, Lilya U., D’yakonov, Vladimir A., Dzhemilev, Usein M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7726926/
https://www.ncbi.nlm.nih.gov/pubmed/33324856
http://dx.doi.org/10.1021/acsomega.0c05072
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author Kadikova, Gulnara N.
Dzhemileva, Lilya U.
D’yakonov, Vladimir A.
Dzhemilev, Usein M.
author_facet Kadikova, Gulnara N.
Dzhemileva, Lilya U.
D’yakonov, Vladimir A.
Dzhemilev, Usein M.
author_sort Kadikova, Gulnara N.
collection PubMed
description [Image: see text] The [6π + 2π] cycloaddition of 2-tropylcyclohexanone to allenes and alkynes was accomplished for the first time using the three-component catalytic system Co(acac)(2)(dppe)/Zn/ZnI(2), thus giving previously unknown functionally substituted bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes in high yields (70–89%). The structures of the synthesized carbocycles were reliably proved using modern spectral methods and X-ray diffraction. The in vitro cytotoxic activity of the obtained bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes against the Jurkat, K562, and U937 tumor cell lines has been studied.
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spelling pubmed-77269262020-12-14 Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone Kadikova, Gulnara N. Dzhemileva, Lilya U. D’yakonov, Vladimir A. Dzhemilev, Usein M. ACS Omega [Image: see text] The [6π + 2π] cycloaddition of 2-tropylcyclohexanone to allenes and alkynes was accomplished for the first time using the three-component catalytic system Co(acac)(2)(dppe)/Zn/ZnI(2), thus giving previously unknown functionally substituted bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes in high yields (70–89%). The structures of the synthesized carbocycles were reliably proved using modern spectral methods and X-ray diffraction. The in vitro cytotoxic activity of the obtained bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes against the Jurkat, K562, and U937 tumor cell lines has been studied. American Chemical Society 2020-11-24 /pmc/articles/PMC7726926/ /pubmed/33324856 http://dx.doi.org/10.1021/acsomega.0c05072 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Kadikova, Gulnara N.
Dzhemileva, Lilya U.
D’yakonov, Vladimir A.
Dzhemilev, Usein M.
Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone
title Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone
title_full Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone
title_fullStr Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone
title_full_unstemmed Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone
title_short Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone
title_sort synthesis of functionally substituted bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes by cobalt(i)-catalyzed [6π + 2π] cycloaddition of 2-tropylcyclohexanone
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7726926/
https://www.ncbi.nlm.nih.gov/pubmed/33324856
http://dx.doi.org/10.1021/acsomega.0c05072
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