56857-90-0

Usage

InChI:InChI=1/C16H12ClNO/c1-18-13-10-6-5-9-12(13)15(17)14(16(18)19)11-7-3-2-4-8-11/h2-10H,1H3

Upstream product

• 519-66-4 4-hydroxy-1-methyl-3-phenylquinolin-2-one 
• 105576-72-5 4-Chloro-1-methyl-3-phenylquinolinium hexafluorophosphate 
• 170956-92-0 N-methyl-2-(2-phenylethynyl)aniline 
• 144603-33-8 3-chloro-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 103-80-0 phenylacetyl chloride 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 83609-72-7 5-Methyl-11-phenyl-isochinolino<4,3-c>chinolin-6(5H)-on 
• 685891-28-5 1-methyl-2-oxo-3-phenyl-1,2-dihydroquinoline-4-carbonitrile 
• 83609-76-1 4-Benzylamino-1-methyl-3-phenyl-chinolin-2(1H)-on 

Relevant academic research and scientific papers

Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides

We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. Calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.

Reaction of some 2-quinolone derivatives with phosphoryl chloride: Synthesis of novel phosphoric acid esters of 4-hydroxy-2-quinolone

3-Chloroquinoline-2,4-diones do not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized by 1H and 13C NMR, IR, EI-MS, and ESI-MS spectroscopy, and in select cases by 31P NMR spectroscopy.

Substituent effects on absorption and fluorescence spectra of carbostyrils

Absorption and fluorescence spectra as well as quantum yields of a series of differently substituted carbostyrils (quinolin-2(1H)-ones) are reported. Especially for compounds containing donor substituents in position 6, substantial bathochromic shifts (comparable to analogous coumarins) of both absorption as well as fluorescence transitions are obtained. High absorption intensities and quantum yields are found for 7-donor substituted isomers. Semiempirical molecular orbital calculations (AMI for structures, ZINDO for electronic transition energies) prove to be a suitable tool for the prediction of absorption and fluorescence properties of these compounds. Ab initio and density functional calculations establish the lactam form as the dominant tautomer of the parent quinolin-2(1H)-one.

Isoquinoquinolones from Phenyl Malonylheterocycles

The reaction of 3-Phenyl-4-hydroxy-2-quinolones (1) and benzylammonium chloride yields the 4-aminocompounds 2 as main products.The isoquino-condensed quinolones 3 are formed as by-products.Thermolysis of 4-benzylamino-2-quinolones (4) affords also 3.Bette