Friedländer reaction on 2-amino-3-cyano-4H-pyrans: Synthesis of derivatives of 4H-pyran [2,3-b] quinoline, new tacrine analogues

Martinez‐Grau, A.; Marco, J. L.

doi:10.1016/s0960-894x(97)10165-2

Cited by 300 publications

(89 citation statements)

References 8 publications

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“…The new molecules (3a-e) were confirmed on the basis of IR, 1 H NMR, 13 C NMR, mass spectral data, and elemental analysis.…”

Section: Chemistrymentioning

confidence: 92%

“…The crude reaction mixture was purified by column chromatography by using ethyl acetate and petroleum ether (1:9, v:v) to give the corresponding products (Scheme 1). 13 13 …”

Section: Methodsmentioning

confidence: 99%

“…IR spectra (KBr) were recorded on a Bruker WM-4(X) spectrometer (577 model). 1 H NMR (300 MHz) and 13 C NMR (75 MHz) spectra were recorded on Bruker AC-300 spectrometer in DMSO- 6 with TMS as an internal standard. Mass spectra (ESI) were recorded on JEOL SX-102 spectrometer.…”

Section: Instrumentationsmentioning

confidence: 99%

“…Chromene derivatives are known to exhibit a wide range of biological activities, such as antifungal, antibacterial [1][2][3][4][5], antioxidative [6], antileishmanial [7], antitumor [8,9], hypotensive [9], antiproliferation [10,11], local anesthetic [12], antiallergenic [13,14], central nervous system activities and effects [15], as well as efficacious in the treatment of Alzheimer's disease [16] and schizophrenia disorder [17]. Coumarins are of scientific interest as anti-HIV agents [18], antituberculosis agents [19], cholinesterase and monoamine oxidase inhibitors [20], antioxidants and anti-inflammatory [21,22].…”

Section: Introductionmentioning

confidence: 99%

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One pot synthesis of substituted 1H-benzo[f]chromen-3-yl-2H-chromen-2-one derivatives

Jagannadham¹,

Ramadevi

Prasanna³

2017

Eur. J. Chem.

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The title compounds, substituted 1H-benzo[f]chromen-3-yl-2H-chromen-2-ones were obtained by reacting 3-aryl-1-(3-coumarinyl)propen-1-ones with 2-napthol catalyzed by DBU (1,8-diazabicyclo[5,4,0]undec-7-ene) and concentrated H2SO4 in ample yields. Their structures were characterized by IR, 1 H NMR, 13 C NMR, mass spectral and elemental analysis. All the synthesized compounds have been evaluated for their in-vitro antibacterial activity against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa and antifungal activity against Aspergillus Niger and Candida albicans by using serial broth dilution method. Among those compounds 3 band 3c exhibits prominent results.

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“…The new molecules (3a-e) were confirmed on the basis of IR, 1 H NMR, 13 C NMR, mass spectral data, and elemental analysis.…”

Section: Chemistrymentioning

confidence: 92%

“…The crude reaction mixture was purified by column chromatography by using ethyl acetate and petroleum ether (1:9, v:v) to give the corresponding products (Scheme 1). 13 13 …”

Section: Methodsmentioning

confidence: 99%

Section: Instrumentationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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One pot synthesis of substituted 1H-benzo[f]chromen-3-yl-2H-chromen-2-one derivatives

Jagannadham¹,

Ramadevi

Prasanna³

2017

Eur. J. Chem.

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“…Chromenes derivatives significant heterocycles that are known to have multiple biological activities 1 for instance, antibacterial, 2 antitumor, 3 sex pheromonal, 4 antimicrobial, 5 TNF-a inhibitory, 6 anticancer, 7 antifungal, 8 estrogenic, 9 antiviral 10 and anti-HIV. 11 Such compounds have also been applied in pigments, and insecticides 12 and therefore, a number of methods and catalysts have been reported for the synthesis of chromene derivatives such as, a [1-(n-butyl)-3-methylimidazolium hydroxide ( 31 Many of the above methods have their own advantages.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ethyl-3-amino-1-aryl-1H-benzo[f]chromeme-2-carboxylate derivatives promoted by DMAP

Zeidanlu¹,

Sheikh²,

Lari³

et al. 2017

10.5267/j.ccl

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An efficient route, convenient and environmentally friendly procedure for the synthesis chromenes derivatives have been developed via a three-component coupling and one-pot reactions of various aromatic aldehyde with malononitrile or ethyl cyanoacetate and phenols in the presence N,N-dimethylpyridin-4-amine (DMAP) in reflux conditions. In simple reaction conditions, the use of DMAP is explored as an easy workup and a green catalyst for the onepot three-component synthesis ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate derivatives.

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Friedländer Condensation

2010

Comprehensive Organic Name Reactions and Reagents

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The preparation of nitrogen‐containing heterocycle (mostly, 2,3‐disubstituted quinolines) from an aromatic ortho ‐aminoaldehyde (or ketone) and an aldehyde (or ketone) bearing an active α‐methylene functionality is regarded to be one of the most successful methods for preparing quinoline derivatives, often in high yield. Therefore, it is generally referred to as the Friedländer condensation, Friedländer synthesis, or Friedländer reaction. The importance of this reaction has been evidenced in the preparation of quinolines, naphthyridines, huprines, and other polycyclic heterocycle derivatives.

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Friedländer reaction on 2-amino-3-cyano-4H-pyrans: Synthesis of derivatives of 4H-pyran [2,3-b] quinoline, new tacrine analogues

Cited by 300 publications

References 8 publications

One pot synthesis of substituted 1H-benzo[f]chromen-3-yl-2H-chromen-2-one derivatives

One pot synthesis of substituted 1H-benzo[f]chromen-3-yl-2H-chromen-2-one derivatives

Synthesis of ethyl-3-amino-1-aryl-1H-benzo[f]chromeme-2-carboxylate derivatives promoted by DMAP

Friedländer Condensation

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