Synthesis and orthogonal functionalization of oxazolo[5′,4′:4,5]pyrano[2,3-b]pyridine by intra- and intermolecular Pd-catalyzed direct C–H bond heteroarylation

Laure Théveau (1) , Cédric Schneider (1) , Olivier Querolle , Lieven Meerpoel , Vincent Levacher (1) , Christophe Hoarau (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The construction and subsequent orthogonal functionalization of a hitherto unknown oxazolo[5′,4′:4,5]pyrano[2,3-b]pyridine are reported. A palladium-catalyzed direct C–H bond functionalization methodology was used to build the tricyclic scaffold as well as to achieve the subsequent C–H bond functionalization at the C-2 position of the oxazole unit with various (hetero)aryl iodides. Remarkably, selective C–H construction and functionalization procedures preserve the chorine atom on the pyridine moiety offering a late-stage substitution site to progress drug design.

Domains: Chemical Sciences

Laure Théveau, Cédric Schneider, Olivier Querolle, Lieven Meerpoel, Vincent Levacher, et al.. Synthesis and orthogonal functionalization of oxazolo[5′,4′:4,5]pyrano[2,3-b]pyridine by intra- and intermolecular Pd-catalyzed direct C–H bond heteroarylation. Organic & Biomolecular Chemistry, 2016, 14 (13), pp.3459-3468. ⟨10.1039/c6ob00227g⟩. ⟨hal-02046242⟩