313822-47-8Relevant academic research and scientific papers
An Efficient Synthesis of (1-Methyl)-2-phenyl-4-quinolones from (N-Methyl)isatoic Anhydride
In Lee, Jae
, p. 556 - 558 (2021)
The acyl substitution of (N-methyl)isatoic anhydride with N,O-dimethylhydroxylamine hydrochloride in CH3CN gave N-methoxy-N-methyl 2-(N-methyl)aminobenzamide, which was treated with ethynyllithium reagents to afford 1-[2-(N-methyl)amino]-3-phen
QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF
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Paragraph 00047-00048, (2022/03/21)
The present invention relates to quinolones of formula (I) and process for its preparation by amine insertion into aryl-ynones thereof. [Formula I] The invention further relates to the process to obtain the natural products such as: graveoline, graveolinine, pseudane IV, pseudane VII, pseudane VIII and pseudane XII. The invention also describes the process for the total synthesis of waltherione F in concise approach from the quinolone synthesized. [Formula II]
Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F
Mehta, Goverdhan,Nerella, Sharanya,Pabbaraja, Srihari,Singh, Shweta
, (2020/02/22)
An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.
4-aminoquinoline compound, and preparation method and application thereof
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Paragraph 0032; 0039-0042, (2019/11/12)
The invention discloses a 4-aminoquinoline compound, and a preparation method and application thereof. The second site of the 4-aminoquinoline compound is replaced by cyclic R-base, the 4-aminoquinoline compound is obtained by 4-step reaction of anthranil
Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles
Lohrer, Bernhard,Bracher, Franz
, (2019/11/26)
Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.
Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes
Xu, Xuefeng,Sun, Ruzhong,Zhang, Sheng,Zhang, Xu,Yi, Wei
supporting information, p. 1893 - 1897 (2018/04/16)
A unique and efficient method for one-pot synthesis of diverse 4-quinolones from simple and readily available primary anilines and alkynes via Cu(I)-catalyzed direct cyclization has been developed. The (thio)phenols were also found to visible substrates for this reaction. Moreover, an unprecedented synthesis of dihydroepindolidiones has been demonstrated by using secondary anilines as the versatile substrates.
One-Pot Allan–Robinson/Friedl?nder Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes
Rai, Vijai K.,Verma, Fooleswar,Sahu, Ganeshwar P.,Singh, Manorama,Rai, Ankita
, p. 537 - 544 (2018/02/09)
The domino synthesis of 2-phenyl-4H-chromen-4-ones and quinolin-4-ones through acetylation of 2-hydroxy-/2-aminobenzaldehydes with α-haloketones followed by intramolecular oxa-/azaheterocyclisation is reported. This method represents a new extension of the Allan–Robinson and Friedl?nder reactions, and uses N-heterocyclic-carbene catalysis to construct the target molecules in good to excellent yields: 86–95 % for the chromen-4-ones, and 83–96 % for the quinolin-4-ones. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by-product formation.
Carbonylative Sonogashira annulation sequence: One-pot synthesis of 4-quinolone and 4H-chromen-4-one derivatives
Ghosh, Prasanjit,Nandi, Aritra Kumar,Das, Sajal
, p. 2025 - 2029 (2018/04/25)
Carbonylative Sonogashira annulation sequence for one pot synthesis of 4-quinolone and 4H-chromen-4-one has been developed in presence of Pd-NHC catalyst. Substituted 2-iodoaniline and 2-iodophenol independently underwent in the carbonylative Sonogashira
Transition-Metal-Free One-Pot Tandem Synthesis of 4-Quinolone and 4 H -Thiochromen-4-one Derivatives Through Sequential Nucleophilic Addition-Elimination-S N Ar Reaction
Wang, Deqiang,Sun, Peng,Jia, Peiyun,Peng, Jinsong,Yue, Yixia,Chen, Chunxia
, p. 4309 - 4320 (2017/09/13)
4-Quinolone and 4 H -thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleo-philic addition of amines or sodium hydrogen sulfide to (Z
Mild, rapid and efficient metal-free synthesis of 2-aryl-4-aryloxyquinolines via direct Csp2[sbnd]O bond formation by using diaryliodonium salts
Nahide, Pradip D.,Solorio-Alvarado, César R.
supporting information, p. 279 - 284 (2017/01/03)
An efficient ligand- and transition metal-free procedure for the direct Csp2[sbnd]O bond formation for the arylation of 2-aryl-4-quinolones was developed. The synthesis of the starting quinolones was carried out under our optimized C
