Pd(0)-Catalyzed Amination in the Synthesis of Bicyclic Compounds Comprising Triazacycloalkane and Fluorophore Moieties

Alexei D. Averin,^a,b@ Nataliya M. Chernichenko,^a Vadim N. Shevchuk,^a Olga A. Maloshitskaya,^a Franck Denat,^c and Irina P. Beletskaya^a,b

^aLomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russia

^bA.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, 119991 Moscow, Russia

^cICMUB UMR6302, CNRS, Université Bourgogne Franche-Comté, 21000 Dijon, France

^@Corresponding author E-mail: alexaveron@yandex.ru

DOI: 10.6060/mhc171255a

Macroheterocycles 2018 11(2) 141-149

Direct introduction of one dansyl fluorophore group into the molecule of 1,4,7-triazacyclononane (TACN) and 1,5,9-triazacyclododecane (TACD) was shown to be possible followed by the modification of triazacycles with two bromobenzyl substituents. The resulting compounds were used in the Pd(0)-catalyzed macrocyclization reaction with 1,13-diaza-4,7,10-trioxatridecane to provide corresponding cryptands. The synthesis of bicyclic derivatives of TACN bearing naphthyl and acridinyl fluorophore groups was accomplished via an alternative procedure using aminal-protected TACN. The possibility to form tetracyclic compounds starting from N,N’,N”-tris(3-bromobenzyl) substituted TACN was demonstrated. Three cryptands bearing dansyl fluorophore were tested as potential fluorescent chemosensors for metal cations and were found to act as molecular fluorescent probes for Cu(II) and Al(III) by total emission quenching in the presence of these cations.

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Pd(0)-Catalyzed Amination in the Synthesis of Bicyclic Compounds Comprising Triazacycloalkane and Fluorophore Moieties

References: