Efficient synthesis of 2-oxazolidinones from epoxides and carbamates catalyzed by amine-functionalized ionic liquids

Abstract

COMMUNICATION This journal isA series of amine-functionalized ionic liquids were prepared and their catalytic performance were tested in the synthesis 2-oxazodinones from epoxides and carbamates. Under optimized reaction conditions, good to excellent yields of various 2-oxazolidinones were achieved with different epoxides and carbamates. Moreoveer, the amine-functionalized ionic liquid catalyst could be easily recovered and reused without significantly loss in activity.

Activated Mn‐MACHO Complexes Form Stable CO2 Adducts

“…Analysis of 1-13 CO 2 (Figure S14) evidences that the N-bound carbon of the CO 2 moiety resonates at δ( 13 C) = 158.63 ppm, which substantially differs from free CO 2 (δ( 13 C) CO2 = 124.79 ppm, Figure S27) and aligns well with values observed for strained carbamates, such as 2-oxazolidinone (δ( 13 C) CO = 161.10 ppm, CDCl 3 ). [12] The infrared (IR) spectrum of 1-CO 2 shows three bands at 1906, 1818 and 1717 cm À 1 attributed to CÀ O stretching modes (Figure 2c). The two highest in energy are assigned to the two carbonyl ligands (cf.…”

Recent Advances in the Synthesis and Ring‐Opening Transformations of 2‐Oxazolidinones

“…In 2015, Shang and co‐workers prepared a series of 2‐oxazolidinones in good to excellent yields under the catalysis of amine‐functionalized ionic liquids (Scheme 38). [61] The conversion of propylene oxide could be enhanced to 90% in the presence of a catalytic amount of triethylamine. To avoid the use of volatile organic amines, a range of amine‐functionalized ionic liquids with various cations and anions 128 – 132 were evaluated: i ‐Pr 2 NEMimCl 128 a was the best choice for this reaction giving the highest conversion of propylene oxide.…”

Synthesis of 9,9-bis(4-hydroxyphenyl) fluorene catalyzed by bifunctional ionic liquids

“… 18,19 Functionalized ILs 20 take advantage of structure design, and can introduce specific functional groups into the cation and/or anion structure of the ILs for specific organic reactions. At present, many functionalized ILs are documented in the literature, and the functionalized groups include sulfonic acid groups, 21,22 hydroxyl groups, 23 alkenyl groups 24 and amino groups 25 etc.…”