98554-71-3

Upstream product

• 1034767-23-1 4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one 
• 623-73-4 diazoacetic acid ethyl ester 
• 95-55-6 2-amino-phenol 
• 88-75-5 2-hydroxynitrobenzene 
• 24265-34-7 2-nitrophenyl 2-chloroacetate 
• 1383579-88-1 C₈H₈ClNO₂ 
• 105-36-2 ethyl bromoacetate 
• 5651-39-8 2H-benzo[b][1,4]oxazin-2-one 

Downstream Products

• 1383579-80-3 C₁₆H₁₅FN₂O₄S 

Relevant academic research and scientific papers

Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds

A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.

Iron-catalyzed oxidative sp3 carbon-hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones

A novel and efficient iron-catalyzed sp3 carbon-hydrogen bond functionalization of benzoxazinone derivatives has been developed. For the first time, benzoxazin-2-ones were used as substrates in an oxidative dehydrogenative coupling reaction. The experiments were performed under mild reaction conditions to construct alkyl-aryl C(sp3)-C(sp2) bonds. The application of this method to the gram-scale synthesis of natural product cephalandole A has been accomplished in a 3-step sequence. A plausible one electron oxidation involved mechanism is proposed.

Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia

Described herein are methods for using compounds that activate pyruvate kinase.

BICYCLIC PKM2 ACTIVATORS

Compounds and compositions comprising compounds including formula (I) that activate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that activate PKM2 in the treatment of cancer.

O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources

Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl, efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give piperazinones and morpholinones and related analogs such as quinoxalinones and benzoxazin-2-ones. This approach provides a new one-pot route for synthesizing these classes of heterocyclic compounds.

A convenient synthesis of 3,4-dihydro-1,4-benzoxazin-2-ones

3,4-Dihydro-1,4-benzoxazin-2-one was prepared for the first time by catalytic hydrogenation of 4-benzyl-3,4-dihydro-1,4-benzoxazin-2-one. A simple and efficient synthesis of 4-benzyl- and 4-alkyl-3,4-dihydro-1,4-benzoxazin-2-one derivatives from ethyl 2-(2-hydroxyphenylamino)acetate and aldehydes is described. Some considerations regarding the reactivity of 3,4-dihydro-1,4-benzoxazin-2-ones are given.