23196-06-7

Upstream product

• 616-45-5 2-pyrrolidinon 
• 529-28-2 4-iodoanisol 
• 95-55-6 2-amino-phenol 
• 578-57-4 2-bromoanisole 
• 67-56-1 methanol 
• 4641-57-0 1-phenylpyrrolidin-2-one 
• 19734-02-2 1-(2-hydroxyphenyl)pyrrolidin-2-one 
• 77-78-1 dimethyl sulfate 
• 96-48-0 4-butanolide 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 208646-50-8 N-(2-methoxyphenyl)-6-aminohexan-3-one 
• 4787-76-2 1-(2-methoxyphenyl)pyrrolidine 

Relevant academic research and scientific papers

Oxone as an inexpensive, safe, and environmentally benign oxidant for C-H bond oxygenation

This paper describes the application of peroxide-based oxidants in the Pd(OAc)2-catalyzed acetoxylation and etherification of arene and alkane C-H bonds. Oxone in acetic acid and/or methanol proved particularly effective, and these transformati

Synthesis of N -Aryl and N -Heteroaryl γ-, δ-, and ?-Lactams Using Deprotometalation-Iodination and N -Arylation, and Properties Thereof

Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl 2 ·TMEDA (M = Zn or Cd; TMEDA = N, N, N ′, N ′-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N -arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using dimethyl sulfoxide as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.

COMPOSITIONS AND METHODS FOR ACYLATING LACTAMS

This disclosure provides methods for intermolecular enantioselective C-acylation of lactams with quaternary stereogenic centers by applying a chiral Ni catalyst. The methods comprise treating a lactam with a chiral Ni catalyst, an aryl nitrile, and an aryl halide.

Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams

A new strategy for catalytic enantioselective C-acylation to generate α-quaternary-substituted lactams is reported. Ni-catalyzed three-component coupling of lactam enolates, benzonitriles, and aryl halides produces β-imino lactams that then afford β-keto lactams by acid hydrolysis. Use of a readily available Mandyphos-type ligand and addition of LiBr enable the construction of quaternary stereocenters on α-substituted lactams to form β-keto lactams in up to 94% ee.

Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water

A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C2O4)·2H2O/N,N′-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.

Copper(I) complexes with trispyrazolylmethane ligands: Synthesis, characterization, and catalytic activity in cross-coupling reactions

Three novel Cu(I) complexes bearing tris(pyrazolyl)methane ligands, Tpmx, have been prepared from reactions of equimolar amounts of CuI and the ligands Tpm, (HC(pz)3), Tpm, (HC(3,5-Me2-pz) 3), and TpmMs, (HC(3-Ms-pz)3). X-ray diffraction studies have shown that the Tpm and TpmMs derivatives exhibit a 2:1 Cu:ligand ratio, whereas the Tpm* complex is a mononuclear species in nature. The latter has been employed as a precatalyst in the arylation of amides and aromatic thiols with good activity. The synthesis of a TpmCu(I)-phthalimidate, a feasible intermediate in this catalytic process, has also been performed. Low temperature 1H NMR studies in CDCl 3 have indicated that this complex exists in solution as a mixture of two, neutral and ionic forms. Conductivity measurements have reinforced this proposal, the ionic form predominating in a very polar solvent such as DMSO. The reaction of TpmCu(I)-phthalimidate with iodobenzene afforded the expected C-N coupling product in 76% yield accounting for its role as an intermediate in this transformation.

Efficient ligand-free copper-catalyzed N-arylation of amides with aryl halides in water

A convenient and efficient protocol has been developed for the cross-coupling of amides and aryl iodides using a ligand-free copper(I) oxide catalyst in water. A variety of amide derivatives afforded the corresponding N-arylated products in moderate to good yields (up to 88%).

1,1,1-Tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols

1,1,1-Tris(hydroxymethyl)ethane was presented as a new, efficient, and versatile tridentate O-donor ligand suitable for the copper-catalyzed formation of C-N, C-S, and C-O bonds. This inexpensive and commercially available tripod ligand has been demonstrated to facilitate the copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols to afford the corresponding desired products in good to excellent yields.

7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridines as novel inhibitors of human eosinophil phosphodiesterase

High-throughput file screening against inhibition of human lung PDE4 led to the discovery of 3-ethyl-1-(4-fluorophenyl)-6-phenyl-7-oxo-4,5,6,7,- tetrahydro-1H-pyrazolo[3,4-c]pyridine (11) as a novel PDE4 inhibitor. Subsequent SAR development, using an eosinophil PDE assay, led to analogues up to 50-fold more potent than 11 with IC50 values of 0.03-1.6 μM. One such compound, CP-220,629 (22) (IC50 = 0.44 μM), was efficacious in the guinea pig aerosolized antigen induced airway obstruction assay (ED50 2.0 mg/kg, po) and demonstrated a significant reduction in eosinophil (55%), neutrophil (65%), and IL-1β (82%) responses to antigen challenge in atopic monkeys (10 mg/kg, po).