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

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/ZnI(2) three-component catalytic system. The reaction gave previously undescribed but promis...

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Autores principales: Kadikova, Gulnara N., D’yakonov, Vladimir A., Dzhemilev, Usein M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8156619/
https://www.ncbi.nlm.nih.gov/pubmed/34069183
http://dx.doi.org/10.3390/molecules26102932
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author Kadikova, Gulnara N.
D’yakonov, Vladimir A.
Dzhemilev, Usein M.
author_facet Kadikova, Gulnara N.
D’yakonov, Vladimir A.
Dzhemilev, Usein M.
author_sort Kadikova, Gulnara N.
collection PubMed
description 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/ZnI(2) 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 ((1)H, (13)C, DEPT (13)C, COSY, NOESY, HSQC, HMBC) NMR spectra.
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spelling pubmed-81566192021-05-28 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 Kadikova, Gulnara N. D’yakonov, Vladimir A. Dzhemilev, Usein M. Molecules Communication 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/ZnI(2) 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 ((1)H, (13)C, DEPT (13)C, COSY, NOESY, HSQC, HMBC) NMR spectra. MDPI 2021-05-14 /pmc/articles/PMC8156619/ /pubmed/34069183 http://dx.doi.org/10.3390/molecules26102932 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Kadikova, Gulnara N.
D’yakonov, Vladimir A.
Dzhemilev, Usein 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
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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8156619/
https://www.ncbi.nlm.nih.gov/pubmed/34069183
http://dx.doi.org/10.3390/molecules26102932
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