Chemo- and Stereoselective Synthesis of Substituted Thiazoles from <i>tert</i>-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts
Srinivasarao Yaragorla, Dandugula Sneha Latha
Abstract
We report here that thioamides can distinguish C–C double bonds and C–C triple bonds chemoselectively when subjected to a reaction with pent-1-en-4-yn-3-ol derivatives in the presence of Ca(OTf)2. This protocol offers a fast, efficient, and high-yielding synthesis of functionalized thiazoles. Interestingly, this reaction offers a time-dependent formation of kinetic and thermodynamic products. The products showed stereoselectivity concerning the alkene geometry. Further, we extended this protocol to synthesize oxazoles from propargyl alcohols and ibuprofen (NSAID) was converted into amide and then subjected to oxazole formation with tert-propargyl alcohols.
Topics & Concepts
AlkyneStereoselectivityAlkeneCatalysisChemistryOrganic chemistryAlkaline earth metalMedicinal chemistryAlkali metalSulfur-Based Synthesis TechniquesSynthesis and Reactivity of Sulfur-Containing CompoundsSynthesis of heterocyclic compounds