1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

A synthetic route to 1,4,6,10-tetraazaadamantanes (TAADs) bearing free and protected amino groups at the bridge N-atoms has been developed via intramolecular cyclotrimerization of C=N units in the corresponding tris(hydrazonoalkyl)amines. In a similar fashion, unsymmetrically substituted TAADs havin...

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Autores principales: Semakin, Artem N, Golovanov, Ivan S, Nelyubina, Yulia V, Sukhorukov, Alexey Yu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9577388/
https://www.ncbi.nlm.nih.gov/pubmed/36300009
http://dx.doi.org/10.3762/bjoc.18.148
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author Semakin, Artem N
Golovanov, Ivan S
Nelyubina, Yulia V
Sukhorukov, Alexey Yu
author_facet Semakin, Artem N
Golovanov, Ivan S
Nelyubina, Yulia V
Sukhorukov, Alexey Yu
author_sort Semakin, Artem N
collection PubMed
description A synthetic route to 1,4,6,10-tetraazaadamantanes (TAADs) bearing free and protected amino groups at the bridge N-atoms has been developed via intramolecular cyclotrimerization of C=N units in the corresponding tris(hydrazonoalkyl)amines. In a similar fashion, unsymmetrically substituted TAADs having both amino and hydroxy groups at the bridge N-atoms were prepared via a hitherto unknown co-trimerization of oxime and hydrazone groups. The use of N-TAAD derivatives as potential ligands and receptors was showcased through forming boron chelates and host–guest complexes with water and simple alcohols.
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spelling pubmed-95773882022-10-25 1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes Semakin, Artem N Golovanov, Ivan S Nelyubina, Yulia V Sukhorukov, Alexey Yu Beilstein J Org Chem Full Research Paper A synthetic route to 1,4,6,10-tetraazaadamantanes (TAADs) bearing free and protected amino groups at the bridge N-atoms has been developed via intramolecular cyclotrimerization of C=N units in the corresponding tris(hydrazonoalkyl)amines. In a similar fashion, unsymmetrically substituted TAADs having both amino and hydroxy groups at the bridge N-atoms were prepared via a hitherto unknown co-trimerization of oxime and hydrazone groups. The use of N-TAAD derivatives as potential ligands and receptors was showcased through forming boron chelates and host–guest complexes with water and simple alcohols. Beilstein-Institut 2022-10-11 /pmc/articles/PMC9577388/ /pubmed/36300009 http://dx.doi.org/10.3762/bjoc.18.148 Text en Copyright © 2022, Semakin et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Semakin, Artem N
Golovanov, Ivan S
Nelyubina, Yulia V
Sukhorukov, Alexey Yu
1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes
title 1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes
title_full 1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes
title_fullStr 1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes
title_full_unstemmed 1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes
title_short 1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes
title_sort 1,4,6,10-tetraazaadamantanes (taads) with n-amino groups: synthesis and formation of boron chelates and host–guest complexes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9577388/
https://www.ncbi.nlm.nih.gov/pubmed/36300009
http://dx.doi.org/10.3762/bjoc.18.148
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