Simple and Expedient Access to Novel Fluorinated Thiazolo- and Oxazolo[3,2-a]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.

Synthesis of Trifluoromethylated Pyrimido[1,2-b]indazole Derivatives through the Cyclocondensation of 3-Aminoindazoles with Ketoester and Their Functionalization via Suzuki-Miyaura Cross-Coupling and SNAr Reactions

“…As part of our on-going effort in the synthesis of novel fluorinated heterocycles [ 27 , 28 , 29 , 30 , 31 ], we report herein a convenient and efficient synthetic strategy that enables the construction of trifluoromethylated pyrimido[1,2- b ]indazole derivatives.…”

“…Therefore, the development of an efficient and facile method to approach fluorinated tricyclic compounds is highly desirable. As part of our on-going effort in the synthesis of novel fluorinated heterocycles [27][28][29][30][31], we report herein a convenient and efficient synthetic strategy that enables the construction of trifluoromethylated pyrimido[1,2-b]indazole derivatives. As part of our on-going effort in the synthesis of novel fluorinated heterocycles [27][28][29][30][31], we report herein a convenient and efficient synthetic strategy that enables the construction of trifluoromethylated pyrimido[1,2-b]indazole derivatives.…”