13oxazol2one

13oxazol2one, also known as 2-oxazolidinone, is a five-membered heterocyclic organic compound. It contains a benzene ring fused to an oxazolidinone ring. The oxazolidinone ring is a five-membered ring containing one oxygen atom, one nitrogen atom, and a carbonyl group. Its chemical formula is C3H5NO2.

2-Oxazolidinone is a white crystalline solid at room temperature. It is soluble in polar organic solvents such as ethanol and dimethyl sulfoxide, and has limited solubility in water. The compound exhibits tautomerism, existing in equilibrium with its enol form.

The primary significance of 2-oxazolidinone lies in its role as a chiral auxiliary in asymmetric synthesis. When attached to a molecule, it can influence the stereochemical outcome of reactions, allowing for the synthesis of specific enantiomers of target molecules. This property makes it valuable in the pharmaceutical industry for the production of chiral drugs.

Derivatives of 2-oxazolidinone are also important. For instance, certain antibiotics, such as linezolid, contain the 2-oxazolidinone moiety and are used to treat infections caused by Gram-positive bacteria. The synthesis of 2-oxazolidinone itself can be achieved through various chemical routes, often involving the cyclization of amino alcohols.