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Issue 104, 2015
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A [two-step/one week] synthesis of C-functionalized homocyclens and cyclams. Application to the preparation of conjugable BCAs without chelating properties alteration

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Abstract

A versatile and efficient bisaminal template approach for the synthesis of cyclam and [13]aneN4 (homocyclen) bifunctional chelating agents (BCAs) bearing a hydroxyethyl function as a C-appended group is presented. The synthesis is rapid (two steps/one week) and does not require fastidious protection–deprotection steps or chromatographic purification. Another reactional route and alternative work-up give access to their oxo-cyclam and oxo-homocyclen analogues. The procedure consists of the cyclization of the preorganized tetraamine 1,4,8,11-tetraazaundecane, in its cis-butanedione-bisaminal form, with an α,β-unsaturated lactone to provide the tetracyclic oxo-intermediate whose bisaminal bridge can be easily removed and/or its amide function reduced under mild conditions. Furthermore, the synthetic route was successfully applied to the synthesis of teta and trita BCAs analogues starting from the linear tetraamine 1,4,7,10-tetraazadecane. Additionally, the appended alcohol functions of various cyclam and homocyclen based ligands were converted into their ethylamine functions following a very convenient procedure. Finally, preliminary analytical and complexation studies highlight that the supplementary hydroxyethyl C-appended chain has only a low impact on the acid–base behaviour and copper(II) or zinc(II) coordination properties of the macrocycle.

Graphical abstract: A [two-step/one week] synthesis of C-functionalized homocyclens and cyclams. Application to the preparation of conjugable BCAs without chelating properties alteration

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Publication details

The article was received on 24 Aug 2015, accepted on 25 Sep 2015 and first published on 25 Sep 2015


Article type: Paper
DOI: 10.1039/C5RA17133D
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Citation: RSC Adv., 2015,5, 85898-85910
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    A [two-step/one week] synthesis of C-functionalized homocyclens and cyclams. Application to the preparation of conjugable BCAs without chelating properties alteration

    N. Camus, Z. Halime, N. le Bris, H. Bernard, M. Beyler, C. Platas-Iglesias and R. Tripier, RSC Adv., 2015, 5, 85898
    DOI: 10.1039/C5RA17133D

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