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

Dedicated to the memory of Prof. Rolf Appel (25 February 1921 – 30 January 2012)
Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis

Abstract

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.

Key words

thiazoloquinazolinone - C–H arylation - palladium - microwave irradiation - Appel’s salt - kinase inhibition

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