Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles

Copper-free click reactions between a dibenzoazocine derivative and azides derived from 5-methyluridine were investigated. The non-catalyzed reaction yielded both regioisomers in an approximately equivalent ratio. The NMR spectra of each regioisomer revealed conformational isomery. The ratio of isom...

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Autores principales: Smyslova, Petra, Popa, Igor, Lyčka, Antonín, Tejral, Gracian, Hlavac, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2015
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4690608/
https://www.ncbi.nlm.nih.gov/pubmed/26673606
http://dx.doi.org/10.1371/journal.pone.0144613
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author Smyslova, Petra
Popa, Igor
Lyčka, Antonín
Tejral, Gracian
Hlavac, Jan
author_facet Smyslova, Petra
Popa, Igor
Lyčka, Antonín
Tejral, Gracian
Hlavac, Jan
author_sort Smyslova, Petra
collection PubMed
description Copper-free click reactions between a dibenzoazocine derivative and azides derived from 5-methyluridine were investigated. The non-catalyzed reaction yielded both regioisomers in an approximately equivalent ratio. The NMR spectra of each regioisomer revealed conformational isomery. The ratio of isomers was dependent on the type of regioisomer and the type of solvent. The synthesis of various analogs, a detailed NMR study and computational modeling provided evidence that the isomery was dependent on the interaction of the azocine and pyrimidine parts.
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spelling pubmed-46906082015-12-31 Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles Smyslova, Petra Popa, Igor Lyčka, Antonín Tejral, Gracian Hlavac, Jan PLoS One Research Article Copper-free click reactions between a dibenzoazocine derivative and azides derived from 5-methyluridine were investigated. The non-catalyzed reaction yielded both regioisomers in an approximately equivalent ratio. The NMR spectra of each regioisomer revealed conformational isomery. The ratio of isomers was dependent on the type of regioisomer and the type of solvent. The synthesis of various analogs, a detailed NMR study and computational modeling provided evidence that the isomery was dependent on the interaction of the azocine and pyrimidine parts. Public Library of Science 2015-12-16 /pmc/articles/PMC4690608/ /pubmed/26673606 http://dx.doi.org/10.1371/journal.pone.0144613 Text en © 2015 Smyslova et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Smyslova, Petra
Popa, Igor
Lyčka, Antonín
Tejral, Gracian
Hlavac, Jan
Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles
title Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles
title_full Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles
title_fullStr Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles
title_full_unstemmed Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles
title_short Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles
title_sort non-catalyzed click reactions of adibo derivatives with 5-methyluridine azides and conformational study of the resulting triazoles
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4690608/
https://www.ncbi.nlm.nih.gov/pubmed/26673606
http://dx.doi.org/10.1371/journal.pone.0144613
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