22445-79-0Relevant academic research and scientific papers
Formation of N-Tributylstannyl-2-oxazolidone from (Bu3Sn)2O and 2-Chloroethyl Isocyanate
Shibata, Ikuya,Baba, Akio,Matsuda, Haruo
, p. 1703 - 1704 (1986)
N-Tributylstannyl-2-oxazolidone is formed from the reaction of (Bu3Sn)2O and 2-chloroethyl isocyanate in the presence of hexamethylphosphoric triamide, and reacts with electrophiles to give N-substituted 2-oxazolidones in good yields.
Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates
Casadei, Maria Antonietta,Moracci, Franco Micheletti,Zappia, Giovanni,Inesi, Achille,Rossi, Leucio
, p. 6754 - 6759 (2007/10/03)
The electrochemical reduction of O2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O2·-/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom ω-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-l,3-oxazm-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the β position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.
Formation of N-Tributylstannyl Heterocycle from Bis(tributyltin) Oxide and ω-Haloalkyl Isocyanate. One-Pot Convenient Synthesis of 2-Oxazolidinones and Tetrahydro-2H-1,3-oxazin-2-one
Shibata, Ikuya,Nakamura, Kenji,Baba, Akio,Matsuda, Haruo
, p. 853 - 859 (2007/10/02)
Novel types of compounds, N-tributylstannyl-2-oxazolidinone (4a) and tetrahydro-2H-1,3-oxazin-2-one (4b), are formed from the adduct of (n-Bu3Sn)2O (1) with ω-haloalkyl isocyanate (2), and the subsequent coupling reaction with alkyl halides gives a variety of N-substituted 2-oxazolidinones and tetrahydro-2-oxazinones in a one-pot procedure.Both the cyclization and the coupling reaction proceed quantitatively in the presence of HMPA which enhances the reactivity of the Sn-heteroatom bond by coordination.
