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A direct method for the N-tetraalkylation of azamacrocycles

Counsell, AJ; Jones, AT; Todd, MH; Rutledge, PJ; (2016) A direct method for the N-tetraalkylation of azamacrocycles. Beilstein Journal of Organic Chemistry , 12 pp. 2457-2461. 10.3762/bjoc.12.239. Green open access

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Abstract

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.

Type: Article
Title: A direct method for the N-tetraalkylation of azamacrocycles
Location: Germany
Open access status: An open access version is available from UCL Discovery
DOI: 10.3762/bjoc.12.239
Publisher version: https://doi.org/10.3762/bjoc.12.239
Language: English
Additional information: This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
Keywords: N-alkylation, azamacrocycles, biphasic system, cyclam, cyclen
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > SoP Pharmaceutical and Bio Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/10057556
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