Brønsted-acid catalyzed cascade annulations toward the fused pyranoquinoline derivatives

Wang, Xiumei; Liu, Mingfan; Chen, Zhiyuan

doi:10.1016/j.tet.2016.06.004

Cited by 14 publications

(5 citation statements)

References 35 publications

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“…The yield was 29%, and rings B and C had identical substituents. Wang et al 28 synthesized a series of similar compounds via acid catalysis starting from an alkyne group, with nitrogen in the ortho position of the ring. The substituents of rings B and C were identical.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds

D’Oliveira

Moura

Moraes

et al. 2018

J. Braz. Chem. Soc.

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Chalcone-quinolinone hybrid compounds, as well as the synthesis of such compounds, have few reports in the literature. Such compounds may be quite useful in therapeutics, since various biological activities are reported for both chalcones and quinolinones. In the present work, several novel chalcone-quinolinone compounds have been synthesized. The reaction conditions developed allowed to obtain the compounds in a single step of synthesis from the chalcones. The products precipitated pure and were isolated by filtration. The yields of such reactions, from 45 to 94%, were promising. The product structures were confirmed by nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS) techniques. Their antitumor activities were evaluated in HCT-116 (colon) cell lines by the 3-(4,5-dimethyl-2-thiazole)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) test. The half maximal inhibitory concentration (IC 50) values obtained for the most active chalcones were between 2.9 and 7.5 and for active quinolinone was 19.3 mg L-1. The antitumor activities results suggest that the class of compounds studied has potential for use in cancer research.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds

D’Oliveira

Moura

Moraes

et al. 2018

J. Braz. Chem. Soc.

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“…Knoevenagel condensation of the second equivalent of aldehyde to the latter gives 152 which in turn treats with malononitrile furnishing the product 153. [109] In the catalyst-free reaction of β-(2-aminophenyl)-α,βynones 57 with nitril oxides 154, a series of isoxazolo [4,5c]quinolines 156 was synthesized through domino [3 + 2] cycloaddition/imination and annulation/aromatization of 155 (Scheme 46). [110] A series of 2-alkoxyfuro[2,3-c]quinoline 163 was synthesized through a catalyst-free three component reaction of 157, aldehydes, and α-(4-nitrophenyl)-α-isocyanoacetate 158.…”

Section: -Alkynylanilines In the Synthesis Of Six-membered Heterocycl...mentioning

confidence: 99%

“…Then, the formed adduct 150 is cyclized to 151 via an intramolecular Michael addition. Knoevenagel condensation of the second equivalent of aldehyde to the latter gives 152 which in turn treats with malononitrile furnishing the product 153 [109] …”

Section: ‐Alkynylanilines In the Synthesis Of Six‐membered Heterocycl...mentioning

confidence: 99%

Annulation of 2‐Alkynylanilines: The Versatile Chemical Compounds

2022

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2-Alkynylanilines as versatile building blocks have been widely applied for the construction of nitrogen atomcontaining heterocycles in organic synthesis. The focus of this review is on the application of 2-alkynylaniline and its derivatives in the metal-catalyzed or metal-free synthesis of various heterocycles including indoles, oxindoles, indazoles, benzisoxazoles, quinolines, benzoxazines, benzothiazines, quinazolines, cinnolines, and seven-and eight-membered heterocycles.

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“…Alternatively, 3‐aryliden‐2,3‐dihydro‐4‐quinolones were accessed through intramolecular acylation of alkenes or alkynes, [4] or palladium‐catalyzed insertion of CO [5] . Although methods for the construction of these valuable heterocyclic compounds have been reported, [6,1d] more attention should be given to develop methods for the synthesis of 3‐aryliden‐2,3‐dihydro‐4‐quinolones, especially develop green as well as economically favourable methods.…”

Section: Introductionmentioning

confidence: 99%

One‐pot Synthesis of 3‐Aryliden‐2,3‐dihydro‐4‐quinolones from o‐Anilinopropargyl Alcohols via Aldol Condensation of In Situ Generated 2,3‐Dihydroquinolin‐4‐ones and Aryl Aldehydes

et al. 2022

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A one-pot conversion of o-anilinopropargyl alcohols to 3-aryliden-2,3-dihydro-4-quinolone derivatives with 20 mol% TfOH as the catalyst has been devised. The method may proceed through a sequential Meyer-Schuster rearrangement of o-anilinopropargyls/intramolecular conjugated addition/aldol condensation of in situ generated 2,3-dihydroquinolin-4-ones and aldehydes. Finally, the subsequent additions succeeded between 3-benzyliden-2,3-dihydro-4-quinolones and hydrazines to give fused multicycles. The reaction is metal-and ligand-free, proceeds under mild conditions, gives high yields, and has a broad substrate scope, making it a valuable method for the construction of 3-aryliden-2,3dihydro-4-quinolone functionalized building blocks.

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Brønsted-acid catalyzed cascade annulations toward the fused pyranoquinoline derivatives

Cited by 14 publications

References 35 publications

Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds

Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds

Annulation of 2‐Alkynylanilines: The Versatile Chemical Compounds

One‐pot Synthesis of 3‐Aryliden‐2,3‐dihydro‐4‐quinolones from o‐Anilinopropargyl Alcohols via Aldol Condensation of In Situ Generated 2,3‐Dihydroquinolin‐4‐ones and Aryl Aldehydes

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