Synthesis of 4-(organoselenyl) oxazolones via cyclization of N-alkynyl ethylcarbamates promoted by organoselenium. Issue 23 (26th May 2022)

• Record Type: Journal Article
• Authors: Goulart, Tales A. C.; Recchi, Ana Maria S.; Back, Davi Fernando; Zeni, Gilson
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 23(2022)
• Page Start: 4773
• Page End: 4781
• Publication Date: 2022-05-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00682k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Organoselenyl iodide promoted the intramolecular nucleophilic cyclization of N -alkynyl ethylcarbamates in the synthesis of 4-(organoselenyl) oxazolones. Abstract : Organoselenyl iodide promoted the intramolecular nucleophilic cyclization of N -alkynyl ethylcarbamates in the synthesis of 4-(organoselenyl) oxazolones. The reaction was regioselective, giving the five-membered oxazolone products as the unique regioisomer via an initial activation of the carbon–carbon triple bond through a seleniranium intermediate, followed by an intramolecular 5- endo-dig cyclization mode. The generality of the methodology has been proven by applying the optimized reaction conditions to different organoselenyl iodides and N -alkynyl ethylcarbamates having different substituents directly bonded to the nitrogen atom and in the terminal position of the alkyne.