Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates

El‐Sheref, Essmat M.; Aly, Ashraf A.; Mourad, Aboul-Fetouh E.; Brown, Alan B.; Bräse, Stefan; Bakheet, Momtaz E. M.

doi:10.1007/s11696-017-0269-6

Cited by 26 publications

(19 citation statements)

References 35 publications

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“…Recently we have synthesized spiro(indoline-3,4′-pyrano[3,2-c]quinoline)-3′-carbonitriles from reaction of quinoline-2,4-diones with 2-(2-oxo-1,2-dihydroindol-3-ylidene)malononitrile (Aly et al, 2018). We also reacted quinolinediones and diethyl acetylene-dicarboxylate to give pyranoquinoline-4-carboxylates and (quinolin-3-yl)fumarates in good yields (El-Sheref et al, 2018). Considering the importance of the interesting chemical behavior of quinolones, and in view of the promising aspects and making a further stepforward we report herein on the application of the one-pot technique in synthesis of the title compounds.…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinates and arylmethylene-bis-3,3′-quinoline-2-ones

et al. 2018

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In this investigation an efficient synthesis of 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinic acid derivatives was achieved by one-pot reaction of one equivalent of aromatic amines with two equivalents of diethyl malonate in diphenyl ether and catalyzed with triethyl amine. In case of applying the previous condition with aromatic amines and diethyl malonate in a ratio of 2:1, no quinolone structure was obtained, whereas N 1 ,N 3-bis(4-bromophenyl)malonamide, as an example, was obtained in 95% yield. Under the same previous condition, arylmethylene-bis-3,3'-quinoline-2-ones were in one pot synthesized via the reaction of equal equivalents of aromatic amines and diethyl malonate together with half equivalent of the corresponding aromatic aldehydes. The structure of the obtained compounds was proved by IR, NMR and mass spectra and X-ray structure analyses.

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Section: Introductionmentioning

confidence: 99%

One-pot synthesis of 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinates and arylmethylene-bis-3,3′-quinoline-2-ones

et al. 2018

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“…On the other hand, quinoline and its analogs represent privileged moieties with numerous derivatives widely distributed in nature . Quinoline plays an important role in the field of synthetic and medicinal chemistry, illustrated by their extensive application as biologically and pharmacologically active compounds, such as antitumor, anti‐parasitic, antimalarial, anti‐hepatitis, antifungals, antimicrobial, anti‐arrythmic, antioxidant, anti‐inflammatory and anticancer properties…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antioxidant and anticholinesterase activities of novel quinoline‐aminophosphonate derivatives

Bazine

Cheraiet

Bensegueni

et al. 2020

Journal of Heterocyclic Chem

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A series of 20 novel α-aminophosphonate derivatives bearing quinoline or quinolone moiety was designed and synthesized via Kabachnik-Fields reaction in the presence of triethylammonium acetate as a solvent and catalyst under ultrasound irradiation. This procedure affords products in high yields and short reaction times. Molecular structures of the synthesized compounds 4a-g and 5a-m were confirmed using various spectroscopic methods. The antioxidant activity of these compounds was evaluated by eight complementary in vitro tests. The anticholinesterase activity (AChE, BChE) of these compounds were also evaluated. In addition, theoretical calculations of all compounds were investigated as corrosion inhibitors using density functional theory (DFT). The results revealed that 16 of these compounds exhibited high levels of antioxidant activities depending on the assay and that most compounds showed more potent inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).H NMR (400 MHz, Chloroform-d 6 ) δ 11.75 (s, 1H, OH), 9.74 (s, 1H, NH), 7.70 (d, J H-P = 3.5 Hz, 1H Ar, H 7 ), 7.10-7.00 (m, 2H Ar, H 1 , H 3, ), 6.93 (dd, J ortho = 8.2, J metha = 1.5 Hz, 1H Ar, H 6 ), 6.88 (dd, J ortho = 7.8, J metha = 1.4 Hz, 1H Ar, H 17 ), 6.72 (td, J ortho = 7.7, J metha = 1.9 Hz, 1H Ar, H 2 ), 6.54 (td, J ortho = 7.6, J metha = 1.4 Hz, 1H Ar, H 18 ), 6.50 (dd, J ortho = 8.4, J metha = 3.6 Hz, 1H Ar, H 16 ), 5.92(d, J = 11.6 Hz, 1H, NH), 5.89(dd, J ortho = 7.8, J metha = 1.7 Hz, 1H, H 15 ), 5.77 (dd, J H-P = 25.0, 11.6 Hz, 1H, H 12 ), 4. 46-4.33 (m, 2H, H 27 ), 4.16-3.91 (m, 2H, H 24 ), 1.20 (t, J = 7.0 Hz, 3H Ar,

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“…In addition, we synthesized several naphtho-1,3-dithiole derivatives [27] and dibenzo[b,i]-thianthrene-5,7,12,14-tetraone derivatives [28]. In our previous studies, we synthesized a series of ethyl pyrano [3,2-c]quinoline-4-carboxylates [29], spiro(indoline-3,4′-pyrano[3,2-c]-quinoline)-3′-carbonitriles [30], 2,3-bis-(4hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinates and arylmethylene-bis-3,3′-quinoline-2ones [31]. In addition to the synthesis of two series of N-2,3-bis(6-substituted-4-hydroxy-2oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-diones and substituted N-(methyl/ ethyl)bisquinolinone triethyl-ammonium, that been reported to inhibit ERK2 activity in an vitro kinase assay [32].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of fused naphthofuro[3,2-c] quinoline-6,7,12-triones and pyrano[3,2-c]quinoline-6,7,8,13-tetraones derivatives as ERK inhibitors with efficacy in BRAF-mutant melanoma

Aly

El‐Sheref

Bakheet

et al. 2019

Bioorganic Chemistry

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Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates

Cited by 26 publications

References 35 publications

One-pot synthesis of 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinates and arylmethylene-bis-3,3′-quinoline-2-ones

One-pot synthesis of 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinates and arylmethylene-bis-3,3′-quinoline-2-ones

Synthesis, antioxidant and anticholinesterase activities of novel quinoline‐aminophosphonate derivatives

Design, synthesis and biological evaluation of fused naphthofuro[3,2-c] quinoline-6,7,12-triones and pyrano[3,2-c]quinoline-6,7,8,13-tetraones derivatives as ERK inhibitors with efficacy in BRAF-mutant melanoma

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