Single-pot reductive conversion of amino acids to their respective 2-oxazolidinones employing trichloromethyl chloroformate as the acylating agent: a multigram synthesis

Hydroxyamination of Olefins Using Br-N-(CO2Me)2

“…The compound was consistent with the previously reported literature data. 27 Solid mp = 132–133 °C; 30 mg; 81% yield; 1 H NMR (500 MHz) (CDCl 3 ) δ 4.19 (1H, dd, J 1 = 8.56, J 2 = 7.09 Hz), 4.74 (1H, t, J = 8.80 Hz), 4.96 (1H, t, J = 7.83 Hz), 5.76 (1H, s, br), 7.31–7.43 (5H, m); 13 C NMR and DEPT (125 MHz) (CDCl 3 ) δ 56.36 (CH), 72.52 (CH 2 ), 126.03 (CH), 128.87 (CH), 129.21 (CH), 139.40 (C), 159.49 (C).…”

Five‐Membered Heterocycles: 1,3‐Azoles

“…Azolidin-2-ones are commonly prepared from aminoalcohols, vicinal diamines and aminothiols by incorporation of a carbonyl unit. Additions to the list of reagents that effect the transformation are bis(trichloromethylcarbonate) [477,478] and trichloromethyl chloroformate [479], which offer the advantages of easier handling and reduced risk of exposure compared to phosgene [480]. Another reagent of choice is carbonyldiimidazole, which by reaction with cysteine affords derivative 304 [Scheme 10.174 (1)] [481].…”

Synthesis of new oxindole derivatives containing oxazolidin-2-one

“…Reaction of amino alcohols with phosgene and related compounds furnishes oxazolidinones. [17][18][19] Also, treatment of amino alcohols with ethyl chloroformate produced carbamates which in turn can be cyclized to 2-oxazolidinones. 20 In continuation of our work on the synthesis of N-substituted isatins, 3,21,22 we herein report the synthesis and characterization of new oxindole derivatives bearing an oxazolidin-2-one sub-unit.…”