Late-Stage C-H Arylation of Thiazolo[5,4- f ]quinazolin-9(8 H)-one Backbone: Synthesis of an Array of Potential Kinase Inhibitors

Florence Couly (1) , Carole Dubouilh-Benard (1) , Thierry Besson (1) , Corinne Fruit (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Driven by the need of structural modification to establish structure-activity relationships, the regioselective C–H bond activation of thiazolo[5,4-f]quinazolin-9(8H)-one backbone has been developed to furnish the corresponding C2-arylated valuable scaffold. This strategy provides a synthetically streamlined and useful route for late-stage diversification of this attractive skeleton, required in drug discovery. A more eco-friendly synthesis of thiazolo[5,4-f]quinazolin-9(8H)-ones is also described giving access to these aforementioned compounds in a facile manner.

Mots clés: Thiazoloquinazolinone; Appel’s salt; C–H arylation; Kinase inhibition; Palladium; Microwave irradiation

Domaines: Chimie

Florence Couly, Carole Dubouilh-Benard, Thierry Besson, Corinne Fruit. Late-Stage C-H Arylation of Thiazolo[5,4- f ]quinazolin-9(8 H)-one Backbone: Synthesis of an Array of Potential Kinase Inhibitors. Synthesis: Journal of Synthetic Organic Chemistry, 2017, 49 (20), pp.4615-4622. ⟨10.1055/s-0036-1588434⟩. ⟨hal-02046272⟩