Synthesis of heterobicyclic tetrakis- and bis-triazenes: Reaction between 3, 3′-ethane-1, 2-diylbis(1, 3, 5-triazabicyclo[3.2.1]octane) (ETABOC) with diazonium salts bearing electron donating groups. (19th January 2021)

• Record Type: Journal Article
• Authors: Rivera, Augusto; González-Salas, Diego; Ríos-Motta, Jaime
• Is Part Of: Tetrahedron letters. Volume 63(2021)
• Publication Date: 2021-01-19
• Subjects: Diazonium -- Bis(imidazolidinyl)-methane -- Bistriazenes -- Tetrakistriazenes -- Aminal cage; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152721
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Reactions described offer a direct route to triazene derivatives. Cyclic aminal are usefull for synthesis of heterobicyclic triazenes. Diazonium coupling reactions with cyclic aminals. Heterobicyclic may have the structural requirement for antitumor activity. Abstract: In this work, a coupling reaction of aryl diazonium salts with a poly- N -nucleophile is developed for the synthesis of a variety of heterobicyclic tetrakis- and bistriazene compounds. The transformation proceeds smoothly in basic medium with good and moderate yields. In addition to the expected 3, 3′-methanediylbis{1, 5-bis[( E )- aryldiazenyl ]-1, 3, 5-triazepanes}, two classes of heterobicyclic bis-triazenes were obtained by two ring rearrangement reactions. Using this method, an unknown class of organic compounds containing the saturated bis(imidazolidinyl)-methane unit can be accessed efficiently.