Simple and Expedient Access to Novel Fluorinated Thiazolo- and Oxazolo[3,2-<i>a</i>]pyrimidin-7-one Derivatives and Their Functionalization via Palladium-Catalyzed Reactions

Abstract

An efficient, versatile, and one-pot method for the preparation of novel fluorinated thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones is described from 2-aminothiazoles or 2-amino-oxazoles and fluorinated alkynoates. This transformation, performed under transition-metal-free conditions, offers new fluorinated cyclized products with good to excellent yields. Moreover, the functionalization of these N-fused scaffolds via the Suzuki-Miyaura and Sonogashira cross-coupling reactions led to the synthesis of highly diverse thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones.

Keywords

• thiazolo[3,2-<i>a</i>]pyrimidin-7-ones
• oxazolo[3,2-<i>a</i>]pyrimidin-7-ones
• fluorinated alkynes
• regioselective
• one-pot reaction
• Suzuki-Miyaura