Convenient Synthesis of Oxazolidinones by the Use of Halomethyloxirane, Primary Amine, and Carbonate Salt

Abstract

[reaction: see text] Primary amines reacted with carbonate salts (Na2CO3, K2CO3, Cs2CO3, and Ag2CO3) and halomethyloxiranes in the presence of a base such as DBU or TEA to give oxazolidinones in high yields. The use of K2CO3 among these carbonate gave the best yield in this synthesis. A reaction mechanism was proposed that the oxazolidinone was obtained from an oxazinanone intermediate via a bicyclo[2.2.1] intermediate. The present reaction can be widely applied to convenient synthesis of useful N-substituted oxazolidinones and chiral oxazolidinones.

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

“…In addition to the examples shown above, several other syntheses of chiral oxazolidinones have also been reported [44][45][46][47][48][49][50][51][52][53]. These include the aminohydroxylation of allylic carbamates [44], catalytic intramolecular aminopalladation [45], polymer supported synthesis and combinatorial synthesis of oxazolidinone libraries [46][47][48], and the conversion of racemic terminal epoxides under kinetic resolution condition [49].…”

Preparation and supporting on solid phase of chiral auxiliary (S)-4-(4hydroxybenzyl)oxazolidin-2-one from L-tyrosinol assisted by Microwaves

“…Entry 1 in 13 Table 1: Compound 3 (0.256 g, 1.26 mmol) was dissolved in anhydrous THF (10 mL), before the addition of TEA (7.14 mmol, 0.726 g) at 0 ºC, and the resulting mixture was stirred for 10 min. A solution of BTC (0.2 g, 0.674 mmol) in 3 mL of THF was added dropwise stirring for 36 h, and then, the mixture was heated to reflux for 1.5 h. The crude product was filtered and washed with 5% aqueous HCl (3 × 5 mL).…”

“…Oxazolidinones have attracted great attention in organic synthesis [8], in the preparation of natural products [9], antibiotics [7], antibacterials [10] and antimicobacterials [11]. In the literature there are reports about the synthesis of these compounds from amino acids and amino alcohols [12], in addition to other substances such as primary [13] and secondary [14] amines, β-lactams [15], aziridines [16], etc.…”

Ionic Liquids-Prompted Synthesis of Biologically Relevant Five- and Six-Membered Heterocyclic Skeletons

“…Recently, some oxazolidinone derivatives such as DUP-105, DUP-721, and linezolid (Zyvox) have attracted much interest as monodrug-or multidrug-resistant antibacterial agents [156]. Recently, some oxazolidinone derivatives such as DUP-105, DUP-721, and linezolid (Zyvox) have attracted much interest as monodrug-or multidrug-resistant antibacterial agents [156].…”