Synthesis of multifunctional 4-hydroxymethyl 2-oxazolidinones from glycidyl carbamate derivatives catalyzed by bicyclic guanidine. (25th May 2021)

• Record Type: Journal Article
• Authors: Yoshida, Yoshiaki; Endo, Takeshi
• Is Part Of: Tetrahedron letters. Volume 72(2021)
• Publication Date: 2021-05-25
• Subjects: Glycidyl carbamate -- 4-Hydroxymethyl 2-oxazolidinone -- Bicyclic guanidine catalyst -- Intramolecular cyclization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153086
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The intramolecular cyclization of glycidyl carbamate to 2-oxazolidinone with several amines at room temperature. Speculated mechanism of intramolecular cyclization of glycidyl carbamate derivatives catalyzed by TBD. Application to multifunctional glycidyl carbamates to achieve bi- and tri-functional alcohols having oxazolidinone moieties. Abstract: 4-Hydroxymethyl 2-oxazolidinones have been successfully synthesized under mild conditions by the intramolecular cyclization of glycidyl carbamate derivatives with a bicyclic guanidine as the efficient catalyst. This reaction system, which is also applicable to the multifunctional compounds, can provide bi- and tri-functional alcohols having oxazolidinone moieties.