114992-53-9Relevant academic research and scientific papers
Synthesis of oxazolidinones from N-aryl-carbamate and epichlorohydrin under mild conditions
Buscemi, Silvestre,Insuasty, Braulio,Marzullo, Paola,Moreno, Leydi Marcela,Piccionello, Antonio Palumbo
, p. 140 - 155 (2022/03/27)
The reaction conditions for an enantiospecific synthesis of various N-aryl-oxazolidinones from N-aryl-carbamates and (R) or (S) epichlorohydrin were optimized. The N-aryl-oxazolidinones were applied to the synthesis of compounds of biological interest such as DuP 721, toloxatone and a linezolid analogue.
A novel and short convergent approach for N-aryl-5-aminomethyl-2- oxazolidinone derivatives Linezolid and DUP-721
Madhusudhan,Om Reddy,Ramanatham,Dubey
, p. 1236 - 1238 (2007/10/03)
A new convergent and short approach for oxazolidinone class of antibacterial agents, Linezolid and DUP-721, has been achieved by condensing 3-chloro-2-((phenoxycarbonyl)oxy) propyl azide with aryl amine followed by reductive acetylation. This one pot approach for N-aryl-5-azidomethyl- 2-oxazolidinone could provide access for rapid preparation of various oxazolidinone analogues.
Synthesis of oxazolidinones by a solid-phase/activation cycloelimination (sp/ace) methodology
Ten Holte, Peter,Van Esseveldt, Bart C. J.,Thijs, Lambertus,Zwanenburg, Binne
, p. 2965 - 2969 (2007/10/03)
A versatile method for the solid-phase synthesis of oxazolidinones is described. An appropriate 1,2-diol is attached to immobilized sulfonyl chloride, resulting in the selective activation of one of the alcohol functions. The subsequent reaction of the ot
Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The 'B' group
Gregory,Brittelli,Wang,Wuonola,McRipley,Eustice,Eberly,Bartholomew,Slee,Forbes
, p. 1673 - 1681 (2007/10/02)
The synthesis and structure/activity studies of the effect of varying the 'B' group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other 'B' functionalities by using S(N)2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different 'B' groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 μg/mL for the most active compounds described.
