Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes

The first crown ether-capped dibenzotetraaza[14]annulenes (DBTAAs), featuring two macrocyclic binding sites fixed in a face-to-face orientation, were synthesized in satisfactory 26–28% isolated yields. Direct N-alkylation of 1,4,10-trioxa-7,13-diazacyclopentadecane by symmetric DBTAA derivatives bea...

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Autores principales: Zwoliński, Krzysztof Miroslaw, Eilmes, Julita
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6423591/
https://www.ncbi.nlm.nih.gov/pubmed/30931003
http://dx.doi.org/10.3762/bjoc.15.57
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author Zwoliński, Krzysztof Miroslaw
Eilmes, Julita
author_facet Zwoliński, Krzysztof Miroslaw
Eilmes, Julita
author_sort Zwoliński, Krzysztof Miroslaw
collection PubMed
description The first crown ether-capped dibenzotetraaza[14]annulenes (DBTAAs), featuring two macrocyclic binding sites fixed in a face-to-face orientation, were synthesized in satisfactory 26–28% isolated yields. Direct N-alkylation of 1,4,10-trioxa-7,13-diazacyclopentadecane by symmetric DBTAA derivatives bearing bromoalkoxy pendants proceed smoothly at a reasonable level of dilution (1.25 mM). The structures were fully characterized by HR-ESIMS, FTIR-ATR, (1)H and (13)C NMR spectroscopy and elemental analysis.
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spelling pubmed-64235912019-03-29 Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes Zwoliński, Krzysztof Miroslaw Eilmes, Julita Beilstein J Org Chem Letter The first crown ether-capped dibenzotetraaza[14]annulenes (DBTAAs), featuring two macrocyclic binding sites fixed in a face-to-face orientation, were synthesized in satisfactory 26–28% isolated yields. Direct N-alkylation of 1,4,10-trioxa-7,13-diazacyclopentadecane by symmetric DBTAA derivatives bearing bromoalkoxy pendants proceed smoothly at a reasonable level of dilution (1.25 mM). The structures were fully characterized by HR-ESIMS, FTIR-ATR, (1)H and (13)C NMR spectroscopy and elemental analysis. Beilstein-Institut 2019-03-11 /pmc/articles/PMC6423591/ /pubmed/30931003 http://dx.doi.org/10.3762/bjoc.15.57 Text en Copyright © 2019, Zwoliński and Eilmes https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Zwoliński, Krzysztof Miroslaw
Eilmes, Julita
Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
title Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
title_full Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
title_fullStr Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
title_full_unstemmed Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
title_short Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
title_sort design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6423591/
https://www.ncbi.nlm.nih.gov/pubmed/30931003
http://dx.doi.org/10.3762/bjoc.15.57
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