52512-26-2

Upstream product

• 513-86-0 3-hydroxy-2-butanon 
• 103-71-9 phenyl isocyanate 
• 52569-43-4 5-methyl-4-methylene-N-phenyl-2-oxazolidinone 

Downstream Products

• 52512-31-9 3a,6a-dimethyl-2,3t,6-triphenyl-(3ar,6ac)-tetrahydro-oxazolo[5,4-d]isoxazol-5-one 
• 1167438-82-5 5,7a-dimethyl-3-phenyl-7,7a-dihydro-3H-benzoxazol-2-one 
• 32446-14-3 2,5-dimethylphenyl(phenyl)amine 
• 1167438-86-9 7a-methyl-3-phenyl-7,7a-dihydro-3H-benzoxazol-2-one 
• 1167438-87-0 3-(7a-methyl-2-oxo-3-phenyl-2,3,7,7a-tetrahydrobenzo[d]oxazol-6-yl)propanal 
• 1205-39-6 N-phenyl-2-methylaniline 
• 1167438-90-5 5-methyl-5-(3-methylbut-2-enyl)-4-methylene-3-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

Regioselective synthesis of N-substituted 4-methylene-2-oxazolidinones and 4-oxazolin-2-ones. Study of reactivity in thermal Michael conjugate additions

N-Substituted 4-methylene-2-isoxazolidinones 9a-9e have been prepared from the tandem condensation of isocyanates 3 with α-ketol 7. In a more polar solvent (DMF) the same reaction led to stereoisomeric alcohols 11 and 12, which could be transformed to the thermodynamically more stable isomers 4-oxazolin-2-ones 10 in good yield. Thermal conjugate additions of both heterocycles 9a and 10a to enone 13 provided the C-5 adduct 15. When the reaction was carried out with the captodative olefin 17, the unexpected aniline 18 was isolated. The regiochemistry of the Michael addition was rationalized in terms of FMO theory by ab initio calculations. (C) 2000 Elsevier Science Ltd.

A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters

A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of a-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used. Wiley-VCH Verlag GmbH & Co. KGaA.