Quinolinone

Lewis-acid-catalyzed Diels-Alder reaction of 3-phenylthio-2- quinolinones with silox-ydiene. Synthesis of the intermediate for dynemicin A core [97]... 

The first step in any of the degradation pathways is the formation of 2-quinolinone/2-hydroxyquinoline/2-oxo-l, 2-dihydroquinoline and quinoline2-oxidoreductase has been shown to be responsible for this initial metabolic reaction [318], When the oxidation is carried out by a dioxygenase, it resulted in the formation of ds-hydrodiol derivatives and when oxidation is carried out by a monooxygenase monohydroxilated derivatives are formed, via the arene oxide intermediates [323],... 

Similarly, treatment of the iV-alkyliminium salts of quinoline under the same oxidizing conditions resulted in formation of l-alkyl-2(2//)-quinolinones 119 (Equation 38) <1996T1451>. 

Quinolinones can be made by the reaction of 2-aminophenones with a ketene ylide via an intramolecular Wittig reaction (Equation 122) <2003JOC4170>. The nucleoside unit in this example survives the reaction conditions. The reaction of (2-fluoromethyl)aniline with esters of arylacetic acid yielded 4-fluorinated 2-quinolinones (Scheme 66) <20040L4061 >. 

Regioselective palladium-catalyzed arylation of ethyl 3-futoate at either the 2- or the 5-position can be achieved by the judicious choice of solvent and palladium catalyst, as shown in Scheme 27. However, efficient arylation requires the use of aryl bromides substituted with electron-withdrawing groups (e.g., NO2) <20030L301>. This method was applied to the synthesis of furo[3,2- ]quinolinone from l-bromo-2-nitrobenzene. 

An efficient one-pot procedure for the synthesis of 4-aryl-8-arylidene-5,6,7,8-tetrahydro-2-quinolinones 66 has been developed by Yen and co-workers [54] based on a cyclocondensation reaction of W-ethoxycarbonylmethylpyridinium chloride with an aromatic aldehyde and cyclohexanone. The microwave-assisted (domestic microwave oven) MCR resulted in the formation of compound 66 in high yields (Scheme 50). 

Yan C-G, Cai X-M, Wang Q-F et al (2008) A novel four component one-pot access to 4, 6-diaryl-2-pyridinone and 4-aryl-5, 6, 7, 8-tetrahydro-2-quinolinones. Lett Org Chem... 

A high-yield preparation of 2- and 4-trifluoromethyl-2-quinolinones was sought. Depending on reaction conditions, the condensation of anilines with ethyl 4,4,4-trifluoroacetoacetate <03S2005> led to two different quinolinones as shown. 

The Buchwald-Hartwig palladium-catalyzed aryl-amino coupling reaction was applied to the synthesis of functionalized A-phenyl-2-quinolinones <03TL4207>. This was especially powerful because known methods of cyclization preclude anilines with electron-withdrawing groups para, or any ortho substituents, for steric reasons. 

The swietenidins A and B, which are the first naturally occurring 2-quinolinones to bear a methoxyl group at C-3, are present in the bark of the East Indian satin wood Chloroxylon swietenia. Their structures, (17) and (18) respectively, were deduced from spectroscopic data... 

L. (2007) Novel selective androgen receptor modulators SAR studies on 6-bisalkylamino-2-quinolinones. Bioorganic el Medicinal Chemistry Letters, 17, 1527-1531. 

Several methods of converting a propynyloxy side-chain into a fused furan ring have been described (see p. 199 for some of them). When this side-chain is attached to a 2-quinolinone, prolonged heating with HMPT and hydrogencar-bonate gives go -to-excellent yields of the furoquinolinone. 

Vinylic isocyanates react with enamines such as 1-pyrrolidino-l-cyclohexene under mild conditions to form a new pyridinone ring and simultaneous loss of pyrrolidine [3S40]. Reaction of an ynaminone with phenyl isocyanate in refluxing THF gives good yields of 3-acyl-4-dimethylamino-2-quinolinone [2056]. A perchloroynamine behaves similarly [2838]. 

A new approach to the synthesis of 3-prenyl-2-quinolinones begins with a 3-carboxymethyl-2-quinolinone and gives a mixture of... 

AI500782 o-Aminocinnamic acid lactam Carbostyril CCRIS 4327 EINECS 200-420-6 a-HydroxyquInoline 2-Hydroxyquinoline NSC 156783 2-Quinolinol 2-Quinolinone a-Quinolone 2-Quinolone 2(1H)-Quinolinone 2(1H)-Quinolone. Crystals mp = 195200 slightly soluble in H20 soluble in EtOH, Et20, HQ. Rutgers Organics GmbH. 

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