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Article Dans Une Revue Tetrahedron Letters Année : 2007

Selective mono N-alkylations of cyclen in one step syntheses

Julien Massue
Sally Plush
  • Fonction : Auteur
Célia Bonnet
Doireann Moore
  • Fonction : Auteur
Thorfinnur Gunnlaugsson
  • Fonction : Auteur

Résumé

In this Letter, we describe selective one step mono N-alkylations of cyclen (1,4,7,10-tetraazacyclododecane) using a range of functionalized alkyl halides. This ‘easy to use’ synthesis gives rise to mono-derivatives of cyclen from various alkyl halides or, when using alkyl dihalides, bis-cyclen derivatives, where the alkyl group links two cyclen macrocycles together. While the reaction conditions require the use of 1:4 stoichiometry (alkyl halide:cyclen), any unreacted cyclen can be recovered with an aqueous extraction and successfully reused. This procedure was found to be quite versatile, being particularly well-suited for cyclen targets bearing protected thiol groups, as well as α-chloroamide-derived chromophores; such cyclen pendant chromophores are employed as antennae for lanthanide luminescence probes and sensors.

Dates et versions

hal-02117736 , version 1 (02-05-2019)

Identifiants

Citer

Julien Massue, Sally Plush, Célia Bonnet, Doireann Moore, Thorfinnur Gunnlaugsson. Selective mono N-alkylations of cyclen in one step syntheses. Tetrahedron Letters, 2007, 48 (45), pp.8052-8055. ⟨10.1016/j.tetlet.2007.09.022⟩. ⟨hal-02117736⟩
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