Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid

Heravi, Majid Μ.; Behbahani, Farahnaz K.; Oskooie, Hossein A.; Shoar, Rahim Hekmat

doi:10.1016/j.tetlet.2005.02.147

Cited by 121 publications

(45 citation statements)

References 22 publications

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“…Usually, secondary and benzyllic substituents are easily dealkylated while primary alkyl groups remain intact. 23 To explain this observation we have proposed a mechanism which is outlined in Scheme 1. As already mentioned, in the first step the complex II is formed by action of SbCl 5 (Lewis acid) on the nitrogen center of 1,4-DHP I.…”

Section: Resultsmentioning

confidence: 99%

Antimony(V) chloride-promoted room temperature aromatization of 1,4-dihydropyridines in non-acidic solvent

Filipan‐Litvic¹,

Litvić²,

Cepanec³

et al. 2008

Arkivoc

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Section: Resultsmentioning

confidence: 99%

Antimony(V) chloride-promoted room temperature aromatization of 1,4-dihydropyridines in non-acidic solvent

Filipan‐Litvic¹,

Litvić²,

Cepanec³

et al. 2008

Arkivoc

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“…The poly-hydroquinolines possessing a bioactive 1, 4-dihydropyridine moiety also have an important biological activities such as vasodilator, bronchodilator, anti-atherosclerotic, antitumor, gero-protective, hepatoprotective and anti-diabetic activity 24 . Although the antioxidant activities of quinolines and 1, 4-dihydropyridines 25,26 have been extensively studied, the poly-hydroquinolines are not well explored.…”

Section: Ijpsr (2018) Volume 9 Issue 1 (Research Article)mentioning

confidence: 99%

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2018

IJPSR

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4-Aryl-hexahydroquinolines in vitro antioxidant properties were evaluated by spectrophotometric method. This method is based on the charge transfer complex which is formed between 4-arylhexahydroquinolines and chloranil. AM1 and PM3 semi empirical methods were used to estimate different physicochemical parameters. The antioxidant activity was correlated with these physicochemical parameters and different QSAR models were generated. Docking studies were also performed in the active site of prenyl transferase to identify the structural features of the antioxidants. Docking scores with appreciable binding energy values also exactly correlated with the experimental activity. The chemscore estimated by Gold Software was found to have a good correlation with the experimental activity. The Docking and QSAR results reveal that the electron donating substituents on benzene ring were responsible to improve the antioxidant activity of the molecules.

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“…[3][4][5] The antioxidants can minimize or inhibit the oxidative damage through interrupting the free-radical formation or terminating the 11 The polyhydroquinolines possessing a bioactive 1,4-dihydropyridine moiety also have important biological properties. [12][13][14] Although the antioxidant activities of quinolines and 1,4-dihydropyridines 15,16 have been extensively studied, the polyhydroquinolines are not well explored. The synthesis and antioxidant evaluation of new polyhydroquinolines, therefore, is included as part of our medicinal chemistry project aiming to identify a new class of antioxidants.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antioxidant evaluation of novel 4-aryl-hexahydroquinolines from lignin

Yang¹,

Zhang²,

Zhou³

et al. 2011

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A series of 4-aryl-hexahydroquinolines were prepared by Hantzsch reaction using aromatic aldehydes obtained from lignin, 1,3-cyclohexanediones, β-ketoesters and ammonium carbonate. The antioxidant properties of compounds 5a-c and 5g-i were evaluated by two methods: scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and scavenging effect on 2,2′-azino-bis(3-ethylenzothiazoline-sulfonic acid) diammonium salt (ABTS + ) radical. The results show that the compounds containing a methoxy moiety exhibit good activities. The study suggests that some synthesized compounds may serve as promising leads for the treatment against tumors or other free radical-related diseases.

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Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid

Cited by 121 publications

References 22 publications

Antimony(V) chloride-promoted room temperature aromatization of 1,4-dihydropyridines in non-acidic solvent

Antimony(V) chloride-promoted room temperature aromatization of 1,4-dihydropyridines in non-acidic solvent

Untitled

Synthesis and antioxidant evaluation of novel 4-aryl-hexahydroquinolines from lignin

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