130721-46-9Relevant academic research and scientific papers
Convenient synthesis of densely functionalized N-substituted 4-methylene-2-oxazolidinone
Kimura
, p. 4887 - 4890 (1990)
O-Propargyl carbamates 1 undergo an intramolecular nucleophilic addition to acetylenic bond at the nitrogen atom to furnish 4-methylene-2-oxazolidinones 2 in good yields in the presence (Cu+ for R1 = p-toluenesulfonyl, Ag+
5-Exo-dig aminocylization/hydroxyfluorination of propargylic carbamates
Arcadi, Antonio,Chiarini, Marco,Del Vecchio, Luana,Marinelli, Fabio
, p. 1 - 13 (2018/04/17)
The unprecedented annulation/hydroxyfluorination of propargylic carbamates to give 4-fluoromethyl-4-hydroxy-oxazolidinones was investigated. The reaction was effectively promoted by NaHCO3 and/or silver catalysis. The peculiar behavior of propa
Convenient synthesis of 4-methylene-2-oxazolidinones and 4-methylenetetrahydro-1,3-oxazin-2-ones via transition-metal catalyzed intramolecular addition of nitrogen atom to actylenic triple bond
Tamaru,Kimura,Tanaka,Kure,Yoshida
, p. 2838 - 2849 (2007/10/02)
2-Propynyl tosylcarbamates 1 undergo cyclization smoothly by the catalysis of CuCl/Et3N or AgNCO/Et3N to furnish 4-methylene-2-oxazolidinones 2 in good yields. The similar cyclization of the N-acyl derivatives of 1 (PhCO, MeCO, EtOCO, etc.) is catalyzed effectively by AgNCO/t-BuOK. These reactions accommodate a variety of substituents at C1 and C3 of 2-propyn-1-ol and provide (Z)-2 as single stereoisomers. The scope of the cyclization of 3-butynyl carbamates is rather limited, and in general only N-tosyl derivatives of terminally unsubstituted 3-butyn-1-ols undergo cyclization to give 4-methylenetetrahydro-1,3-oxazin-2-ones in synthetically useful yields by the catalysis of AgNCO/Et3N or AgNCO/t-BuOK.
