99553-83-0

Upstream product

• 28172-58-9 2-p-methoxyphenyl-4-phenyl-2-oxazolin-5-one 
• 2835-06-5 phenylglycin 
• 28172-53-4 DL-2-(4-methoxybenzamido)-2-phenylacetic acid 

Downstream Products

• 110698-99-2 4-[1-(4-Chloro-phenyl)-1H-[1,2,3]triazol-4-ylmethyl]-2-(4-methoxy-phenyl)-4-phenyl-4H-oxazol-5-one 
• 122409-86-3 4-[1-(4-Chloro-phenyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-ylmethyl]-2-(4-methoxy-phenyl)-4-phenyl-4H-oxazol-5-one 

Relevant academic research and scientific papers

Catalytic Aerobic Cross-Dehydrogenative Coupling of Azlactones en Route to α,α-Disubstituted α-Amino Acids

We developed a catalytic aerobic method to synthesize α,α-disubstituted α-amino acids through cross-dehydrogenative coupling of azlactones. Combining an iron catalyst with a bisoxazolidine ligand resulted in high catalytic performance, and cross-coupling with an indole proceeded smoothly under aerobic conditions. A wide variety of α-aryl and aliphatic amino acid derived azlactones were applied to the present catalysis. In addition, a quaternary carbon could be constructed using oxindole and benzofuranone under aerobic conditions.

Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer

A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.

Chemoselective activation of sp3 vs sp2 C-H bonds with Pd(II)

The first selective coupling of a carbon nucleophile with methyl, ethyl, propyl, and butyl arenes in the absence of a directing group is described. Pd(OAc)2 double C-H activation displays remarkable selectivity for the terminal methyl sites in alkyl arenes, rather than the more commonly observed arene sp2 C-H activation. Mechanistic studies indicate the intermediacy of an azlactone dimer, obtained from oxidation with Pd(OAc)2, and are consistent with a Pd-catalyzed C-H activation vs a radical process. The observed reactivity establishes that typical reaction solvents (e.g., toluene) can readily participate in C-H activation chemistry.

OXIDATION OF MESOIONIC OXAZOLONES BY OXYGEN

The reaction of molecular oxygen with several 2,4-disubstituted oxazolones (3a-3g) is studied in the present paper.It is shown that oxygen may induce oxidative dimerization to dehydrodimers (7a-7g) via the mesoionic form of the oxazolone.The equilibration

GENERATION AND FATE OF FREE RADICALS OF Δ2-OXAZOLIN-5-ONES

The reaction of Δ2-oxazolin-5-ones 1a and 1b with nickel peroxid in benzene produces the corresponding 4,4-dehydrodimers 5a and 5b as the main products in yields over 75percent.Under the same conditions, the 2-aryl-4-methyl-Δ2-oxazolin-5-ones 1c, 1d and 1e yield five products.In the case of 1c, the constituents of the product mixture were separated and identified as two 4,4-dehydrodimers (meso and dl pair isomers) 5c and 5c', (40.7percent), 2,4-dehydrodimer 6c (34.9percent), acetylanisoylimide 8c(8.5percent) and anisamide (15.9percent).Adequate mechanistic schemes are discussed to account for the products formed.