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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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046242
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:37:28 PM
Last modification on : Thursday, July 2, 2020 - 3:29:21 AM

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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 and Biomolecular Chemistry, Royal Society of Chemistry, 2016, 14 (13), pp.3459-3468. ⟨10.1039/c6ob00227g⟩. ⟨hal-02046242⟩

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