A direct method for the N-tetraalkylation of azamacrocycles

An efficient protocol for the direct synthesis of N-tetraalkylated derivatives of the azamacrocycles cyclam and cyclen has been developed, using a partially miscible aqueous–organic solvent system with propargyl bromide, benzyl bromide, and related halides. The method works most effectively when the...

Descripción completa

Detalles Bibliográficos
Autores principales: Counsell, Andrew J, Jones, Angus T, Todd, Matthew H, Rutledge, Peter J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238601/
https://www.ncbi.nlm.nih.gov/pubmed/28144313
http://dx.doi.org/10.3762/bjoc.12.239
_version_ 1782495734693625856
author Counsell, Andrew J
Jones, Angus T
Todd, Matthew H
Rutledge, Peter J
author_facet Counsell, Andrew J
Jones, Angus T
Todd, Matthew H
Rutledge, Peter J
author_sort Counsell, Andrew J
collection PubMed
description An efficient protocol for the direct synthesis of N-tetraalkylated derivatives of the azamacrocycles cyclam and cyclen has been developed, using a partially miscible aqueous–organic solvent system with propargyl bromide, benzyl bromide, and related halides. The method works most effectively when the reaction mixture is shaken, not stirred. A crystal structure of the N-tetrapropargyl cyclam derivative 1,4,8,11-tetra(prop-2-yn-1-yl)-1,4,8,11-tetraazacyclotetradecane diperchlorate is reported.
format Online
Article
Text
id pubmed-5238601
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-52386012017-01-31 A direct method for the N-tetraalkylation of azamacrocycles Counsell, Andrew J Jones, Angus T Todd, Matthew H Rutledge, Peter J Beilstein J Org Chem Letter An efficient protocol for the direct synthesis of N-tetraalkylated derivatives of the azamacrocycles cyclam and cyclen has been developed, using a partially miscible aqueous–organic solvent system with propargyl bromide, benzyl bromide, and related halides. The method works most effectively when the reaction mixture is shaken, not stirred. A crystal structure of the N-tetrapropargyl cyclam derivative 1,4,8,11-tetra(prop-2-yn-1-yl)-1,4,8,11-tetraazacyclotetradecane diperchlorate is reported. Beilstein-Institut 2016-11-18 /pmc/articles/PMC5238601/ /pubmed/28144313 http://dx.doi.org/10.3762/bjoc.12.239 Text en Copyright © 2016, Counsell et al. 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), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Counsell, Andrew J
Jones, Angus T
Todd, Matthew H
Rutledge, Peter J
A direct method for the N-tetraalkylation of azamacrocycles
title A direct method for the N-tetraalkylation of azamacrocycles
title_full A direct method for the N-tetraalkylation of azamacrocycles
title_fullStr A direct method for the N-tetraalkylation of azamacrocycles
title_full_unstemmed A direct method for the N-tetraalkylation of azamacrocycles
title_short A direct method for the N-tetraalkylation of azamacrocycles
title_sort direct method for the n-tetraalkylation of azamacrocycles
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238601/
https://www.ncbi.nlm.nih.gov/pubmed/28144313
http://dx.doi.org/10.3762/bjoc.12.239
work_keys_str_mv AT counsellandrewj adirectmethodforthentetraalkylationofazamacrocycles
AT jonesangust adirectmethodforthentetraalkylationofazamacrocycles
AT toddmatthewh adirectmethodforthentetraalkylationofazamacrocycles
AT rutledgepeterj adirectmethodforthentetraalkylationofazamacrocycles
AT counsellandrewj directmethodforthentetraalkylationofazamacrocycles
AT jonesangust directmethodforthentetraalkylationofazamacrocycles
AT toddmatthewh directmethodforthentetraalkylationofazamacrocycles
AT rutledgepeterj directmethodforthentetraalkylationofazamacrocycles

Ejemplares similares