One-pot synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by ytterbium perfluorooctanoate [Yb(PFO)3]

Tang, Jun; Wang, Limin; Yao, Yin‐Fang; Zhang, Liang; Wang, Wenbo

doi:10.1016/j.tetlet.2010.11.102

Cited by 93 publications

(35 citation statements)

References 20 publications

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“…Among the pyridine ring systems which present varied chemotherapeutic and pharmacological applicabilities [4][5][6], 2-amino-3-cyanopyridines raised substantial medicinal and synthetic attentionssince this widespread heterocycle molecules allowed an access to many demonstrated bio-active species such as IKK-b inhibitors [7], A 2A adenosine receptor antagonist [8], and potent inhibitor of HIV-1 integrase [9]. Hence, in consequence of the aforementioned biological significances of these versatile structural motifs, a number of procedures have been reported on this topic like microwave or ultrasound irradiation [10][11][12][13], hexadecyldimethyl benzyl ammonium bromide and triethylamine [14], DMF [15], acetic acid [16], Fe 3 O 4 [17], Cellulose-SO 3 H [18]and using earth Lewis acid catalyst [19]. Although, several catalyst and protocol have been studied for the preparation of the 2-amino-3-cyanopyridine derivatives, the methods suffer from one or more imperfection such as toxic solvent like benzene [20], multi-steps reaction pathway [21], high temperature and microwave assistance [22,23], prolonged reaction times and harsh reaction conditions with low yields.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical studies of the nanostructured {Fe₃O₄@SiO₂@(CH₂)₃Im}C(CN)₃catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

et al. 2016

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Rad a 2-Amino-4,6-diphenylnicotinonitriles were prepared by using Fe3O4@SiO2@(CH2)3Im}C(CN)3 as a nanostructured catalyst with an ionic liquid tag under solvent free and benign conditions. Experimental evidences and theoretical studies confirmed that the final step of the synthetic pathway is proceeded via an anomeric based oxidation mechanism. A good range of aromatic aldehydes were condensed with acetophenone derivatives, malononitrile and ammonium acetate to afford their corresponding products in short reaction times and good to high yields.

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Section: Introductionmentioning

confidence: 99%

Experimental and theoretical studies of the nanostructured {Fe₃O₄@SiO₂@(CH₂)₃Im}C(CN)₃catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

et al. 2016

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“…To establish, the generality of this methodology, we used various substituted benzaldehydes to obtain (7a-g). All compounds were known and their structures were confirmed by comparison of physical and spectral data with those of already reported (Table 7) [58][59][60]. A proposed mechanism for the nano-Fe 3 O 4 -catalyzed formation of 2-amino-3-cyano derivatives is shown in Scheme 3.…”

Section: Resultssupporting

confidence: 53%

Using magnetic nanoparticles Fe3O4 as a reusable catalyst for the synthesis of pyran and pyridine derivatives via one-pot multicomponent reaction

et al. 2015

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In recent years, several methods and developments have been reported for the synthesis of pyran and pyridine [13][14][15][16][17] derivatives; each has its own merits and drawbacks. Many of the standard procedures require long reaction times, harsh reaction conditions, expensive and toxic reagents, solvents, and tedious work-up procedures. Moreover in some cases, a mixture of products is obtained, needing cost-effective column chromatography, naturally resulting in low yields. Heterogeneous catalysis is of supreme importance in many areas of the chemical and energy consuming industries [18,19].Conducting the reactions, using heterogenous catalysts should compensate some of drawbacks observed in previously reported reactions. In this kind of reaction, the catalyst can be separated by filtration. However, it is worthy to mention in spite of several advantages, experienced, practically in using of heterogenous catalysts, due to the nanosized particles used, few limitations to the sustainability are observed [20].To get around these problems, the use of a heterogeneous catalyst which can be separated practically other than filtration is desirable. Magnetite nanoparticles (Fe 3 O 4 ) have attracted much attention in the past decade, due to their unique features, including, low preparation cost, high thermal and mechanical stability, and adaptability for largescale production. In addition, their paramagnetic nature allows their facile and effective separation from the reaction mixture, without using standard filtration, required in separation of heterogeneous catalysts. Magnetite nanoparticles (Fe 3 O 4 ) can be easily separated from reaction mixture by using just an external magnet [21].Thus, in recent years, nano-Fe 3 O 4 [22] has attracted a great attention as heterogeneous catalyst [23] due to its simple handling, easy of recovery with an external magnetic field [24,25]. Magnetic nanoparticles (MNPs) have Abstract An atom-economical, efficient and mild protocol is described for the synthesis of 2-amino-3-cyanopyridine and 2-amino-3-cyano-4H-pyran derivatives in the presence of high surface area Fe 3 O 4 as a highly effective heterogeneous catalyst via one-pot multicomponent cyclocondensation reaction.

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“…The structure of (+)-nopinone was confirmed by FT-IR, 1 H NMR and ESI-MS, and values were in good agreement with those reported in the literature [18] . Multicomponent reaction has been widely used in the synthesis of 2-amino-3-cyanopyridine [19,20] . Compared with the common reaction method [21] , multicomponent reaction is more facile, effective and economical.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…For the four component reaction between an aldehyde, a ketone, malononitrile and ammonium acetate, earlier 16 (m, 1H, -CH-), 1.34 (s, 3H, -CH 3 Table 2 IC 50 values of (+)-nopinone-based 2-amino-3-cyanopyridines against three human cancer cell lines studies have found that para-substituted and metasubstituted aromatic aldehydes tolerated the reaction and yielded considerable products, but ortho-substituted aromatic aldehydes only gave trace products [19] . However, in this study, we successfully obtained relevant products using ortho-substituted aromatic aldehydes by the one-pot four-component reactions (compounds 4b and 4c).…”

Section: Synthesismentioning

confidence: 99%

Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

Liao¹,

Shang²,

Shen³

et al. 2015

Front. Agr. Sci. Eng.

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Twelve (+)-nopinone-based 2-amino-3-cyanopyridines 4a-l were synthesized from (-)-β-pinene. The structures of these compounds were characterized by FT-IR, 1 H NMR, and ESI-MS. All the compounds were tested for their anticancer activity against lung cancer cell line A549, gastric cancer cell line MKN45 and breast cancer cell line MCF7 by MTT method, respectively. The results showed that compounds 4f, 4j and 4k had promising anticancer activity against these cancer cell lines, in particular, compound 4f exhibited broad-spectrum and highly efficient anticancer activity against cell lines A549, MKN45 and MCF7 with IC 50 of 23.78, 67.61 and 53.87 µmol$L -1 , respectively. The preliminary analysis of the structure activity relationship implied that the Br or Cl substituted group of the benzene ring in these derivatives significantly contributed to the anticancer activity.

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One-pot synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by ytterbium perfluorooctanoate [Yb(PFO)3]

Cited by 93 publications

References 20 publications

Experimental and theoretical studies of the nanostructured {Fe₃O₄@SiO₂@(CH₂)₃Im}C(CN)₃catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

Experimental and theoretical studies of the nanostructured {Fe₃O₄@SiO₂@(CH₂)₃Im}C(CN)₃catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

Using magnetic nanoparticles Fe3O4 as a reusable catalyst for the synthesis of pyran and pyridine derivatives via one-pot multicomponent reaction

Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

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One-pot synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by ytterbium perfluorooctanoate [Yb(PFO)3]

Cited by 93 publications

References 20 publications

Experimental and theoretical studies of the nanostructured {Fe3O4@SiO2@(CH2)3Im}C(CN)3catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

Experimental and theoretical studies of the nanostructured {Fe3O4@SiO2@(CH2)3Im}C(CN)3catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

Using magnetic nanoparticles Fe3O4 as a reusable catalyst for the synthesis of pyran and pyridine derivatives via one-pot multicomponent reaction

Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

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Experimental and theoretical studies of the nanostructured {Fe₃O₄@SiO₂@(CH₂)₃Im}C(CN)₃catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

Experimental and theoretical studies of the nanostructured {Fe₃O₄@SiO₂@(CH₂)₃Im}C(CN)₃catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation