Synthesis of novel carboranyl azides and “click” reactions thereof

Publication date: Available online 31 October 2019Source: Journal of Organometallic ChemistryAuthor(s): Marina Yu. Stogniy, Svetlana A. Erokhina, Anna A. Druzina, Igor B. Sivaev, Vladimir I. BregadzeAbstractNovel nido-carboranyl azide [7-N3CH2CH2OCH2CH2O-7,8-C2B9H11]- was prepared by the reaction of 1-hydroxy-ortho-carborane with bis(2-chloroethyl) ether followed by the conversion to its nido-form and reactions with sodium iodide and sodium azide. Previously undescribed carboranyl azides 1-N3CH2CH2OCH2CH2S-1,2-C2B10H11 and [7-N3CH2CH2OCH2CH2S-7,8-C2B9H11]- were synthesized by alkylation of trimethylammonium salt of 1-mercapto-ortho-carborane with bis(2-chloroethyl) ether followed by reactions with sodium iodide and with sodium azide and by the conversion of closo-derivative to water soluble nido-form. closo- and nido-Carboranyl azides 1-N3CH2CH2OCH2CH2S-1,2-C2B10H11 and [7-N3CH2CH2OCH2CH2S-7,8-C2B9H11]- were used for the copper(I)-catalyzed azide-alkyne cycloaddition with phenyacetylene. The compounds prepared can be used for the copper(I)-catalyzed сonjugation with biomolecules that act as tumor-targeting vectors for radionuclide diagnostics and boron neutron capture therapy of cancer.Graphical abstract
Source: Journal of Organometallic Chemistry - Category: Chemistry Source Type: research