25410-99-5

Upstream product

• 183382-99-2 C₁₇H₁₇NO₂ 
• 124856-99-1 (2-Amino-phenyl)-((2S,3R)-3-phenyl-oxiranyl)-methanone 
• 577-59-3 2-acetylnitrobenzene 
• 16619-38-8 2'-nitro-chalcone 
• 24220-92-6 1-benzylquinolin-4(1H)-one 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 1258792-52-7 1-benzyl-3-phenylquinolin-4(1H)-one 
• 69511-68-8 2,3-epoxy-1-(2-nitrophenyl)-3-phenyl-1-propanone 
• 529-37-3 4(1H)-quinolinone 
• 100-63-0 phenylhydrazine 
• 551-93-9 2-aminoacetophenone 
• 78396-00-6 2-aminochalcone 
• 124856-99-1 2'-Aminochalcone Epoxide 
• 107-31-3 Methyl formate 

Downstream Products

• 1186060-55-8 allyl 4-oxo-3-phenylquinoline-1(4H)-carboxylate 
• 1258792-52-7 1-benzyl-3-phenylquinolin-4(1H)-one 
• 6319-32-0 4-chloro-3-phenylquinoline 
• 1258792-41-4 1,3-diphenylquinolin-4(1H)-one 
• 56857-96-6 1-methyl-3-phenylquinolin-4(1H)-one 

Relevant academic research and scientific papers

Substrate or Solvent-Controlled PdII-Catalyzed Regioselective Arylation of Quinolin-4(1H)-ones Using Diaryliodonium Salts: Facile Access to Benzoxocine and Aaptamine Analogues

Regioselective C3, C5, and C8 arylation of quinolin-4(1H)-ones have been accomplished either by substrate-control or by tuning the reaction solvent. A variety of aryl(mesityl)iodonium triflates could smoothly deliver arylated products in good to excellent yields. Additionally, it offers great flexibility by arylating medicinally potent quinolone related heterocycles such as acridin-9(10H)-one, and phenanthridin-6(5H)-one under standard reaction conditions. This strategy was further extended with diphenyleneiodonium triflate to access oxacine fused quinolines. The post-modifications of synthesized products enhance the further utility of this protocol in organic synthesis. To the best of our knowledge, this is the first report on C5 arylation of quinolin-4(1H)-ones using iodine(III) reagents.

Construction of azaisoflavone derivatives by hypervalent iodine reagent-mediated oxidative rearrangement of 2'-nitrochalcone

Fabrication of a synthetic azaisoflavone skeleton from 2'-nitrochalcone was done using oxidative rearrangement with a hypervalent iodine reagent. A key intermediate compound, aminoacetal, was prepared from readily available 2'-nitrochalcone via a PhI(OH)O

Efficient construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides

An efficient method for construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides has been developed. The practical approach is of excellent functional groups compatibili

Transition-Metal-Free C-3 Arylation of Quinoline-4-ones with Arylhydrazines

(Chemical Equation Presented) A transition-metal-free C-3-arylation of quinolin-4-ones in the presence of base has been achieved by using arylhydrazines as aryl radical source and air as oxidant. The reaction proceeds smoothly at room temperature and does

Azaisoflavones: Synthesis, antimicrobial evaluation and binding affinity with DNA gyrase

Antimicrobial potency of azaisoflavones has been evaluated in vitro against nine bacterial and two fungal strains, respectively. The requisite azaisoflavones are conveniently synthesized in three steps, with the key step being the super acid catalyzed tandem reaction. The biological results reveal that out of twelve compounds screened, 3 compounds (5a, 5j and 5l) exhibited comparable activities against the standard drugs and demonstrated activities at μM concentration. In addition, molecular docking revealed that compound 5a as the most potent by showing a least binding energy of -5.99 kcal/mol with DNA gyrase receptor compared to other compounds.

Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy

A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.

Palladium-catalyzed oxidative carbonylation for the synthesis of polycyclic aromatic hydrocarbons (PAHs)

A direct and facile palladium-catalyzed C-H bond oxidative carbonylation reaction and oxidative cyclization for the synthesis of polycyclic aromatic hydrocarbons (PAHs) is reported herein. The intramolecular cyclocarbonylation, through C-H activation and C-C, C-O bond formations under mild conditions, proceeds smoothly with good functional group tolerance in high to excellent yields. The intramolecular palladium-catalyzed direct oxidative C-H bond functionalization for the C-O bond formation is also demonstrated, which provides an efficient approach for the construction of various PAHs.

Triflic acid promoted tandem ring-closure-aryl-migration of 2-amino chalcone epoxide: A new synthetic route to azaisoflavones

An unprecedented TfOH-promoted tandem ring-closure-aryl-migration of 2′-amino chalcone epoxide leading to 3-aryl-4(1H)-quinolones (azaisoflavones) was achieved. The outcome of the reaction was confirmed by NMR analysis and rationalized through the intermediacy of a phenonium ion. This synthetic protocol furnishes azaisoflavones straightforwardly from simple starting materials under mild conditions. Georg Thieme Verlag Stuttgart New York.

Catalytic asymmetric alkylation of substituted isoflavanones

The asymmetric alkylation of isoflavanones (3-aryl-chroman-4-ones) and protected 3-phenyl-2,3-dihydroquinolin-4(1H)-ones catalyzed by a novel cinchonidine-derived phase transfer catalyst E is reported. This functionalization occurs at the unactivated C3 methine to afford novel products that can easily be functionalized to generate more complex fused ring systems. The process accommodates a variety of isoflavanones and activated electrophiles and installs a stereogenic quaternary center in high yield and with good-to-excellent selectivity. Isoflavanones are a privileged class of natural products with a broad spectrum of biological activities including insecticidal, antimicrobial, antibacterial, estrogenic, antitumor, and anti-HIV activity. 1 Isoflavanones are also precursors for more complex natural products such as pterocarpans and rotenones.1 Given their therapeutic promise, selective strategies to access new classes of isoflavanones and related structures has high value.2 The functionalization of the C3 position could promote beneficial interactions with biological targets of interest. Specifically, an alkylation at C3 can rapidly access new members of the general class of biologically active homoisoflavanones.3

Pharmaceutical compositions comprising 4-quinolones for treating cancers

A non-cytotoxic pharmaceutical composition acting on the proliferation of clonogenic cells in malignant tumors and including an efficient amount of a compound selected among the compounds of formula (I) and (Ia).