A1 Refereed original research article in a scientific journal
Preparation of hexaaza and heptaaza macrocycles functionalized with a single aminoalkyl pendant arm
Authors: Zhang ZB, Mikkola S, Lonnberg H
Publisher: ROYAL SOC CHEMISTRY
Publication year: 2003
Journal: Organic and Biomolecular Chemistry
Journal name in source: ORGANIC & BIOMOLECULAR CHEMISTRY
Journal acronym: ORG BIOMOL CHEM
Volume: 1
Issue: 5
First page : 854
Last page: 858
Number of pages: 5
ISSN: 1477-0520
DOI: https://doi.org/10.1039/b210663a
Abstract
A practical and reproducible route for the preparation of 1,4,7,10,13,16,19-heptaazacyclohenicosane (1) 1,4,7,10,13,16-hexaazacyclooctadecane (2), and 1,4,7,10,13,17-hexaazacycloicosane (3) bearing a single N-(2-aminoethyl) pendant arm has been developed. Richman-Atkins cyclization in the presence of caesium carbonate was applied to construct the macrocycle from 3-benzoyl-N-1 ,N-5-ditosyl-3-azapentane-1,5-diamine and the appropriate fully N-tosylated N-alpha,N-omega-bis(2-mesyloxyethyl) tri- or tetra-amine. The benzoyl group was selectively removed with potassium tert-butoxide, and the exposed nitrogen atom was reacted with N-tosylaziridine. The tosyl protections were removed with hydrogen bromide in acetic acid, and the product was converted to a free base with the aid of a strong anion exchange resin (OH- form).
A practical and reproducible route for the preparation of 1,4,7,10,13,16,19-heptaazacyclohenicosane (1) 1,4,7,10,13,16-hexaazacyclooctadecane (2), and 1,4,7,10,13,17-hexaazacycloicosane (3) bearing a single N-(2-aminoethyl) pendant arm has been developed. Richman-Atkins cyclization in the presence of caesium carbonate was applied to construct the macrocycle from 3-benzoyl-N-1 ,N-5-ditosyl-3-azapentane-1,5-diamine and the appropriate fully N-tosylated N-alpha,N-omega-bis(2-mesyloxyethyl) tri- or tetra-amine. The benzoyl group was selectively removed with potassium tert-butoxide, and the exposed nitrogen atom was reacted with N-tosylaziridine. The tosyl protections were removed with hydrogen bromide in acetic acid, and the product was converted to a free base with the aid of a strong anion exchange resin (OH- form).
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