32606-02-3

Usage

InChI:InChI=1/C11H11NO2/c1-7-10(13)8-5-3-4-6-9(8)12(2)11(7)14/h3-6,14H,1-2H3

Upstream product

• 88187-53-5 2-Methyl-3-(2-methylamino-phenyl)-3-oxo-propionic acid ethyl ester 
• 17583-40-3 2-methylaminobenzonitrile 
• 106888-31-7 N-(2-bromopropionyl)-N-methyl-2-cyanoaniline 
• 80675-53-2 1-ethoxy-1-trimethylsiloxyprop-1-ene 
• 10328-92-4 N-Methylisatoic anhydride 
• 773837-37-9 sodium cyanide 
• 91349-09-6 3-chloro-1,3-dimethyl-1H-quinoline-2,4-dione 
• 67-56-1 methanol 
• 609-08-5 Diethyl methylmalonate 
• 100-61-8 N-methylaniline 
• 1399323-83-1 1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxoquinolin-3-yl thiocyanate 
• 1885-29-6 anthranilic acid nitrile 
• 85-91-6 Methyl N-methylanthranilate 
• 1264-45-5 (2RS)-methylmalonyl-CoA 

Downstream Products

• 1447565-30-1 1,3-dimethyl-5,6-diphenylpyrano[2,3,4-de]quinolin-2(1H)-one 
• 1416969-71-5 3-[(3E)-5-(4-chlorophenyl)-5-oxopent-3-en-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroquinoline-2,4-dione 
• 50333-13-6 N-methylflindersine 
• 80356-44-1 4-amino-1,3-dimethylquinolin-2(1H)-one 
• 80356-46-3 4-Benzylamino-1,3-dimethyl-1H-quinolin-2-one 
• 32606-05-6 2-N-methylaminophenyl isopropyl ketone 

Relevant academic research and scientific papers

Reactions of heterocyclic quinone methides: 1-Methyl-3-methylene-2,4(1H,3H)-quinolinedione

1-Methyl-3-methylene-2,4(1H,3H)-quinolinedione (2), prepared from 4-hydroxy-1,3-dimethyl-2(1H)-quinolinone (1) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) gives the dimer 3. Compound 2 also reacts in situ with 2,2-dimethyl-2H-1-benzopyran and with isopropenyl acetate to give Diels-Alder cycloaddition products.

Metal-Free Organoselenium-Enabled Radical Relay Azidation-Carbocyclization

An organoselenium-enabled radical relay Azidation-carbocyclization reaction for the preparation of azide-substituted quinoline-2,4-diones was developed. A series of previously unknown structurally diverse azide- substituted quinoline-2,4-diones were obtai

Reaction of Tertiary 2-Chloroketones with Cyanide Ions: Application to 3-Chloroquinolinediones

3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

Catalyst-controlled divergent C-H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds with alkynes and alkenes

Achieving site-selective, switchable C-H functionalizations of substrates that contain several different types of reactive C-H bonds is an attractive objective to enable the generation of different products from the same starting materials. Herein, we dem

Enantioselective copper(I)-Catalyzed borylative aldol cyclizations of enone diones

Pina colato? In the presence of a chiral CuI/bisphosphine complex and B2(pin)2, enone diones undergo diastereo- and enantioselective desymmetrization to deliver highly functionalized bicyclic products. The products can be

Modified riemschneider reaction of 3-thiocyanatoquinolinediones

The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H2SO4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds. Copyright

Modified mukaiyama reaction for the synthesis of quinoline alkaloid analogues: Total synthesis of 3,3-diisopentenyl-N-methylquinoline-2,4-dione

A general synthetic approach, capable of accessing a diverse range of 3,3-disubstituted quinoline-2,4-diones and 1,8-naph-thyridine-2,4-diones via titanium tetrachloride catalyzed C-acylation of silyl ketene acetals is described. The suggested methodological platform is surveyed using different reaction conditions and is applied to the total syntheses of 3,3-diisopentenyl-N-methylquinoline-2,4-dione and 3-demethyl-N-methylatanine.

Enzymatic formation of quinolone alkaloids by a plant type III polyketide synthase

(Chemical Equation Presented) Benzalacetone synthase from Rheum palmatum efficiently catalyzed condensation of N-methylanthraniloyl-CoA (or anthraniloyl-CoA) with malonyl-CoA (or methylmalonyl-CoA) to produce 4-hydroxy-2(1H)-quinolones, a novel alkaloidal scaffold produced by a type III polyketide synthase (PKS). Manipulation of the functionally divergent type III PKSs by a nonphysiological substrate thus provides an efficient method for production of pharmaceutically important quinolone alkaloids.

Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations

Coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolin-2(1H)-ones can be conveniently prepared by treatment of α-halocarboxylic acid esters of salicylaldehyde, o-hydroxyacetophenone, methyl salicylate, and methyl N-methyl- or N-phenylanthranilates with sodium or lithium telluride. Phenylketene formation competes with cyclization of the α-chlorophenylacetate ester of methyl salicylate as demonstrated by a trapping experiment with benzylamine. Elemental tellurium may be recovered and reused.