Synthesis of oxazolidinones from N-aryl-carbamate and epichlorohydrin under mild conditions

Piccionello, Antonio Palumbo; Moreno, Leydi M.; Marzullo, Paola; Buscemi, Silvestre; Insuasty, Braulio

doi:10.24820/ark.5550190.p011.706

Cited by 3 publications

(1 citation statement)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,2 The high reactivity of the three-membered ring provides the use of ECH to obtain di-and trifunctional organic compounds, polyfunctional polymers, and composites based on them 2,3 to develop effective methods for the synthesis of new heterocyclic and macrocyclic molecules. [4][5][6][7][8][9] The reactions of epichlorohydrin with proton-containing reagents (carboxylic acids, alcohols, phenols) are widely used for the synthesis of biologically active substances that exhibit antibacterial, antituberculous, and antimalarial properties, act as antioxidants and enzyme inhibitors, and are included to hypoglycemic drugs. 1,[10][11][12] The oxirane ring opening by carboxylic acids occurs to form two regioisomeric chlorohydrin esters (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Finding the right balance between tertiary amine steric effect and solvent polarity for the regioselectivity and kinetics of epichlorohydrin acetolysis

Yutilova,

Tkach,

Tarasenko

et al. 2023

J of Physical Organic Chem

View full text Add to dashboard Cite

The asymmetric oxirane ring‐opening reaction leading to the formation of regioisomeric chlorohydrin esters was studied in the reaction series “acetic acid–epichlorohydrin–tetrahydrofuran (nitrobenzene)–trialkylamine” by kinetic methods and FT‐IR spectroscopy. The effect of solvent polarity and the structure of tertiary amines on the regioselectivity and reaction rate were studied. Tertiary amines with comparable basicity but different nucleophilicity and spatial structure were chosen as catalysts. It was shown that in solvents of different polarity, the components of the initial reaction system are present both as hydrogen‐bonded complexes and as individual substances. The reaction orders with respect to acid and amine in solvents of different polarity were established. Correlations between the reaction rate and the parameters of nucleophilicity and structure of amines as well as the polarity of the solvent were established. The regioselectivity of the reaction was studied by 1H NMR spectroscopy using the ratio of regioisomeric reaction products. It was shown that the regioselectivity and rate of catalytic acetolysis of epichlorohydrin are effectively controlled by the structure of tertiary amines and the polarity of the solvent. The scheme of reaction regio‐flows was detailed.

show abstract

Section: Introductionmentioning

confidence: 99%

Finding the right balance between tertiary amine steric effect and solvent polarity for the regioselectivity and kinetics of epichlorohydrin acetolysis

Yutilova,

Tkach,

Tarasenko

et al. 2023

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

Rapidly Diverse Synthesis of N‐Aryl‐5‐Substituted‐2‐Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates

Lin,

Chang,

Chiou

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

The method for converting epoxy carbamates to oxazolidinones is outlined in this study. This innovative approach combines intermolecular nucleophilic epoxide ring opening with intramolecular acyl substitution in a single step, thereby facilitating rapid conversion. Significantly, this method effectively addresses challenges associated with the use of expensive reagents, harsh reaction conditions, and prolonged reaction times, presenting a more efficient alternative. Demonstrating favorable reactivity across a diverse range of aryl groups, as well as benzyl or tert‐butyl carbamates, the method consistently yields satisfactory results, with oxazolidinone formation ranging from 55% to 99% in over 24 examples. The synthesized oxazolidinones, including 5v–5x, hold substantial promise as intermediates for the synthesis of crucial synthetic molecules. Furthermore, the versatility of this method is underscored by its successful application in the formation of the 6‐membered ring 1,3‐oxazinan‐2‐one. These findings not only contribute to the advancement of synthetic methodologies but also pave the way for a streamlined synthesis of important pharmaceutical compounds.

show abstract

Kevlar® and Nomex® modification via 2,4-dihydroxybenzophenone anchoring improves water repellency and induces antibacterial and UV protection properties

Tonis,

Frousiou,

Heliopoulos

et al. 2023

Materials Today Chemistry

View full text Add to dashboard Cite

Synthesis of oxazolidinones from N-aryl-carbamate and epichlorohydrin under mild conditions

Cited by 3 publications

References 41 publications

Finding the right balance between tertiary amine steric effect and solvent polarity for the regioselectivity and kinetics of epichlorohydrin acetolysis

Finding the right balance between tertiary amine steric effect and solvent polarity for the regioselectivity and kinetics of epichlorohydrin acetolysis

Rapidly Diverse Synthesis of N‐Aryl‐5‐Substituted‐2‐Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates

Kevlar® and Nomex® modification via 2,4-dihydroxybenzophenone anchoring improves water repellency and induces antibacterial and UV protection properties

Contact Info

Product

Resources

About