175355-72-3

Upstream product

• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 175355-70-1 1-(methoxymethyl)-3,4-dihydroquinolin-2(1H)-one 
• 175355-71-2 1-Methoxymethyl-3-phenylsulfanyl-1H-quinolin-2-one 
• 144-48-9 iodacetamide 
• 930-69-8 sodium thiophenolate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 939-16-2 3-bromoquinolin-2-one 
• 108-98-5 thiophenol 
• 5332-24-1 3-bromoquinoline 
• 22615-00-5 3-bromoquinoline N-oxide 

Downstream Products

• 175355-74-5 2-Oxo-3-phenylsulfanyl-2H-quinoline-1-carboxylic acid methyl ester 
• 175355-73-4 Carbonic acid methyl ester 3-phenylsulfanyl-quinolin-2-yl ester 

Relevant academic research and scientific papers

Enantioselective Synthesis of Diaryl Sulfoxides Enabled by Molecular Recognition

The enantioselective sulfoxidation of diaryl-type sulfides was accomplished using a chiral manganese porphyrin complex equipped with a remote molecular recognition site. Despite the marginal size difference between the two substituents at the prostereogen

Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions

An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44–99 %) and with significant enantiomeric excess (70–99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.

One-pot copper-catalyzed three-component reaction: A modular approach to functionalized 2-quinolones

A copper-catalyzed three-component annulation for the synthesis of functionalized 2-quinolones was developed. Three reactions including an SN2, a Knoevenagel, and finally C-N bond formation are involved in the designed cascade reaction using 2-bromoacylarenes, 2-iodoacetamide, and nucleophiles as the three components. A new catalytic system was discovered during the study and this modular approach is highly efficient to access functionalized 2-quinolone derivatives, compatible with a broad range of functional groups, scalable, and step-economic. Further derivatization of the obtained product demonstrates the synthetic utility of this method.

Lewis acid catalyzed Diels-Alder reaction of 3-phenylthio-2-quinolinones with siloxydiene. Synthesis of the intermediate for dynemicin A core

Preparation of the 1-methoxycarbonyl-3-phenylthio-2-quinolinone (10) from dihydro-2-quinolinone (5) and its Diels-Alder reaction with 2- trimethylsilyloxy-1,3-butadiene under Lewis acid catalyst is described. Conversion of the D-A adduct (11) to 9-phenant