Synthesis of N-substituted-4-methylene-oxazolidinones via base-catalyzed cyclization of propargylic alcohols with p-toluenesulfonyl isocyanate. Issue 9 (September 2020)

• Record Type: Journal Article
• Authors: Pi, Shao-Feng; Guo, Yue-Meng; Zhou, Zheng-Rui; Sun, Han-zhou; Yi, Bing
• Is Part Of: Journal of chemical research. Volume 44:Issue 9/10(2020)
• Page Start: 521
• Page End: 523
• Publication Date: 2020-09
• Subjects: base-catalyzed -- cyclization -- oxazolidinones -- propargylic alcohols -- p-toluenesulfonyl isocyanate; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.1177/1747519820907304
• Languages: English
• ISSNs: 1747-5198

Abstract

A practical method is developed for the synthesis of oxazolidinone derivatives, an important class of heterocyclic compounds. The effect of bases and solvents on this cyclization reaction is discussed and a simple new base–solvent system (triethylamine in toluene) is found to be the most effective. The reaction conditions developed here are mild and no by-products are observed. Moreover, using optimized conditions, a number of differently substituted propargylic alcohols are cyclized to the corresponding N -substituted-4-methylene-oxazolidinones in yields of up to 99%.