A novel metal-free synthesis of thiazole-substituted α-hydroxy carbonyl compounds and 2-alkenylthiazoles from thiazole N-oxides and olefins. Issue 51 (19th December 2019)

• Record Type: Journal Article
• Authors: Li, Hui; Zhang, Juan; Zhang, Yanqiu; Wang, Jiayi; Song, Gonghua
• Is Part Of: Tetrahedron letters. Volume 60:Issue 51(2019)
• Publication Date: 2019-12-19
• Subjects: Metal-free -- Thiazole N-oxide -- 1, 3-Dipolar cycloaddition -- Thiazole-substituted α-hydroxy carbonyl; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.05.053
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A metal-free and atom-economic synthesis of thiazole-substituted α-hydroxy carbonyl compounds has been established. A domino 1, 3-dipolar cycloaddition and ring-opening aromatization reaction was involved. The corresponding 2-alkenylthiazoles were produced in excellent yields through a one-pot, two-step dehydration process. Abstract: A metal-free and highly atom-economic synthesis of thiazole-substituted α-hydroxy carbonyl compounds has been developed. Catalyzed by 5 mol% of p -toluenesulfonic acid (TsOH), a variety of thiazole-substituted α-hydroxy carbonyl compounds were obtained in moderate to good yields via 1, 3-dipolar cycloaddition of thiazole N -oxides with olefins, followed by a ring-opening reaction. Furthermore, the corresponding 2-alkenylthiazoles could be produced in excellent yields from synthesized α-hydroxy carbonyl compounds through a one-pot, two-step dehydration process.