5259-97-2

Usage

Uses

1,3-Oxazinan-2-one is a reactant used in the preparation of HIV integrase inhibitors active against raltegravir resistant strains.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 3, p. 84, 1966 DOI: 10.1002/jhet.5570030118

InChI:InChI=1/C4H7NO2/c6-4-5-2-1-3-7-4/h1-3H2,(H,5,6)

Upstream product

• 868-84-8 S,S-dimethyl dithiocarbonate 
• 156-87-6 propan-1-ol-3-amine 
• 57-13-6 urea 
• 504-63-2 trimethyleneglycol 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 

Downstream Products

• 100060-82-0 2-oxo-dihydro-[1,3]oxazine-3-carboxylic acid anilide 
• 5467-84-5 1,3-diphenethylurea 
• 105910-76-7 N-(3-hydroxy-propyl)-N'-phenethyl-urea 
• 56535-85-4 3,4,5,6-tetrahydro-1-phenylpyrimidin-2(1H)-one 
• 31792-19-5 3-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-benzoyl]-[1,3]oxazinan-2-one 
• 56017-71-1 1-(5,6-dihydro-4H-[1,3]oxazin-2-yl)-pyridinium; toluene-4-sulfonate 
• 18370-81-5 (3-bromopropyl)amine 
• 83708-45-6 N-phenyl-1,3-propanediamine dihydrochloride 
• 2038-57-5 3-Phenylpropan-1-amine 
• 18655-50-0 3-(4-chlorophenyl)propylamine 
• 18655-48-6 3-(2-chlorophenyl)propan-1-amine 
• 54930-39-1 3-(4-methylphenyl)propanamine 
• 76293-74-8 3-(2-Methylphenyl)propylamine 
• 1069112-05-5 4-(2-nitrophenyl)-1-(2-oxo-[1,3]oxazinan-3-yl)-butane-1,3-dione 

Relevant academic research and scientific papers

PROCESS FOR THE SYNTHESIS OF ISOCYANATE-FREE OMEGA-HYDROXY-URETHANES, ALPHA-OMEGA-DIURETHANES AND OLIGO (POLY)URETHANES

The synthesis of omega-hydroxyalkyl-urethanes, and of alfa-omega-diurethanes is reported which includes the reaction of diols with urea in presence of catalysts based on Ce at temperatures between 125 and 170°C over 4-8 h reaction time. A process for the production of oligomers of omega-hydroxyalkyl-urethanes is also reported based on the reaction of urea with diols in presence of Ce or Zr catalysts or Ce mixed oxides at 125-170°C over 4-20 h.

Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and solvent

Urea derivatives are obtained in mild to good yield from the reactions of primary aliphatic amines with CO2 in the absence of any catalysts, organic solvents or other additives. To optimize reaction conditions, experimental variables including temperature, pressure, the concentration of amine, reaction time etc. were studied. Satisfactory yields were obtained at the optimized conditions that are comparable to the presence of catalyst and solvent. The preliminary investigation of the reaction mechanism showed that alkyl ammonium alkyl carbamate was quickly formed as the intermediate, and then the final product was formed by the intramolecular dehydration.

Pd-catalysed oxidative carbonylation of amino alcohols to N,N′-bis(hydroxyalkyl)ureas under mild conditions using molecular oxygen as the oxidant

A very simple method has been developed for the selective synthesis of symmetrical N,N′-bis(hydroxyalkyl)ureas, OC[NH-(CH2)x-OH]2 (x = 3-6), by oxidative carbonylation of α,ω-amino alcohols [3-aminopropanol (3-AP), 4-aminobutanol (4-AB), 5-aminopentanol (5-APe), 6-aminohexanol (6-AH)] with CO/O2 mixtures (O2 = 5 mol%) in the presence of Pd(II)/ligand/NEt3·HI catalytic systems. The catalytic process takes place under very mild conditions (p(CO/O2) = 0.1 MPa; 303-333 K). The target products can be isolated in high yield through a very simple and straightforward procedure. The catalytic system can be easily recovered and recycled for several times. The influence of a few reaction parameters (nature of ancillary ligand and iodide co-catalyst, I/Pd molar ratio, etc.) on the catalytic activity has also been investigated and the main mechanistic features of the catalytic process fully elucidated.

Formation of Cyclic Urethanes from Amino Alcohols and Carbon Dioxide Using Phosphorus(III) Reagents and Halogenoalkanes

Cyclic urethanes are obtained in good yields under mild conditions from amino alcohols and carbon dioxide using phosphorus(III) reagents and halogenoalkanes (CCl4 and CCl3CCl3).

A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM

Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.