Synthesis of Halogenated Dibenzo[1,2,6]triazonines and Late-Stage Functionalization of the Triazonine Ring
Résumé
Dibenzotriazonine is a new class of nine-membered cyclic azobenzenes, with a nitrogen atom embedded in the bridging chain. To enable future applications of this photoactive backbone, we propose in this study the synthesis of mono and dihalogenated triazonines, that allow the late-stage introduction of different functionalized aryl groups and heteroatoms (N, O, P) via palladium-catalyzed reactions. Indeed, different diphenylphosphoryl-triazonines were synthesized with functional groups such as carbamate or phenol. Bis(diphenylphosphoryl)phenyl-mono-and bis-carbamate-triazonines were also isolated in good yields.
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