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Pd-Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides

Abstract : A selective functionalization of thiazolo[5,4-f]quinazolin-9(8H)-one has been developed through sequential activation of C–H bonds to furnish diarylated compounds. This strategy allows the regioselective C2 and C7 arylation by a judicious choice of coupling partners and bases, requiring no additional ligands or directing groups. Differently substituted N8-benzylated-2,7-diaryl-thiazoloquinazolin-9(8H)-ones were thereby obtained in a facile manner. A one-pot procedure was also performed. These protocols provide a synthetically useful route for late-stage functionalization of this highly valuable scaffold, required in drug discovery.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046211
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:36:40 PM
Last modification on : Thursday, July 2, 2020 - 3:28:51 AM

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Marine Harari, Florence Couly, Corinne Fruit, Thierry Besson. Pd-Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides. Organic Letters, American Chemical Society, 2016, 18 (13), pp.3282-3285. ⟨10.1021/acs.orglett.6b01552⟩. ⟨hal-02046211⟩

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