Knoevenagel Condensation Reaction Using Ionic Liquid [ADPQ][CF3SO3] as Green and Reusable Catalyst

Gao, Xiaochong; Gao, Can; Gao, Ruichang

doi:10.14233/ajchem.2015.17821

Cited by 4 publications

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“…It should be mentioned that 2-(1 H -indol-2-yl)-3-acrylonitriles 2a [ 59 , 60 , 61 , 62 , 63 ] and 2b [ 61 , 62 , 63 ] have been previously reported. However, there have been no reports of their biological activities.…”

Section: Resultsmentioning

confidence: 99%

“…197–199 °C (m.p. 173–174 °C [ 63 ]); IR ν max (KBr, cm −1 ): 3360, 3085, 3058, 3023, 2224, 1433, 1341, 1302, 914, 782, 726, 676; 1 H NMR (300 MHz, DMSO- d 6 ) δ (ppm): 11.74 (s, 1H, NH), 7.92 (s, 1H, CH), 7.87 (d, J = 7.1 Hz, 2H, 2 × C-H arom ), 7.62–7.45 (m, 4H, 4 × C-H arom ), 7.41 (d, J = 8.9 Hz, 1H, C-H arom ), 7.18 (t, J = 7.1 Hz, 1H, C-H arom ), 7.04 (t, J = 7.5 Hz, 1H, C-H arom ), 6.80 (s, 1H, C 3 -H, indole); 13 C NMR (75 MHz, DMSO- d 6 ) δ (ppm): 138.6, 138.2, 134.0, 133.7, 130.9, 129.6 (two overlapping signals), 129.2 (two overlapping signals), 128.2, 123.9, 121.3, 120.4, 117.5, 111.8, 104.2, 103.7; MS (ESI) m / z : 243 [M − H] − . Anal.…”

Section: Methodsmentioning

confidence: 99%

“…Yield: 62% (yellow solid); m.p. 223–224 °C (192–194 °C [ 63 ]); IR ν max (KBr, cm −1 ): 3356, 3045, 2918, 2223, 1611, 1435, 1302, 898, 798, 782, 730, 607; 1 H NMR (400 MHz, DMSO- d 6 ) δ (ppm): 11.72 (s, 1H, NH), 7.90 (s, 1H, CH), 7.80 (d, J = 8.2 Hz, 2H, 2 × C-H arom ), 7.60 (d, J = 7.9 Hz, 1H, C-H arom ), 7.43–7.37 (m, 1H, C-H arom ), 7.38 (d, J = 8.0 Hz, 2H, 2 × C-H arom ), 7.20 (t, J = 7.0 Hz, 1H, C-H arom ), 7.05 (t, J = 7.0 Hz, 1H, C-H arom ), 6.79 (s, 1H, C 3 -H, indole), 2.39 (s, 3H, CH 3 ); MS (ESI) m / z : 257 [M − H] − . Anal.…”

Section: Methodsmentioning

confidence: 99%

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Indole-Acrylonitrile Derivatives as Potential Antitumor and Antimicrobial Agents—Synthesis, In Vitro and In Silico Studies

et al. 2023

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A series of 2-(1H-indol-2-yl)-3-acrylonitrile derivatives, 2a–x, 3, 4a–b, 5a–d, 6a–b, and 7, were synthesized as potential antitumor and antimicrobial agents. The structures of the prepared compounds were evaluated based on elemental analysis, IR, 1H- and 13NMR, as well as MS spectra. X-ray crystal analysis of the representative 2-(1H-indol-2-yl)-3-acrylonitrile 2l showed that the acrylonitrile double bond was Z-configured. All compounds were screened at the National Cancer Institute (USA) for their activities against a panel of approximately 60 human tumor cell lines and the relationship between structure and in vitro antitumor activity is discussed. Compounds of interest 2l and 5a–d showed significant growth inhibition potency against various tumor cell lines with the mean midpoint GI50 values of all tests in the range of 0.38-7.91 mM. The prominent compound with remarkable activity (GI50 = 0.0244-5.06 mM) and high potency (TGI = 0.0866-0.938 mM) against some cell lines of leukemia (HL-60(TB)), non-small cell lung cancer (NCI-H522), colon cancer (COLO 205), CNS cancer (SF-539, SNB-75), ovarian cancer ((OVCAR-3), renal cancer (A498, RXF 393), and breast cancer (MDA-MB-468) was 3-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-indol-2-yl)acrylonitrile (5c). Moreover, the selected 2-(1H-indol-2-yl)-3-acrylonitriles 2a–c and 2e–x were evaluated for their antibacterial and antifungal activities against Gram-positive and Gram-negative pathogens as well as Candida albicans. Among them, 2-(1H-indol-2-yl)-3-(1H-pyrrol-2-yl)acrylonitrile (2x) showed the most potent antimicrobial activity and therefore it can be considered as a lead structure for further development of antimicrobial agents. Finally, molecular docking studies as well as drug-likeness and ADME profile prediction were carried out.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Indole-Acrylonitrile Derivatives as Potential Antitumor and Antimicrobial Agents—Synthesis, In Vitro and In Silico Studies

et al. 2023

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“…The calculations suggest that acetic anhydride reacts with the lone pair of the 17-amine above the D ring to generate an acylium salt 9, whereas acetylation of the free form 1 proceeds on the primary amine at position 14 to produce 2. 8 On the basis of these results, we postulated the reaction mechanism by which compounds 3 and 4 are formed. The possible reaction mechanism for the formation of 3, as shown in Scheme 4, depicts an intramolecular reaction between acylium carbon linked to the 17-nitrogen and the 14-nitrogen to produce amidinium salt 11 via 10.…”

mentioning

confidence: 94%

“…In the stable conformation of the 14-amino group-protonated form, the hydrogen bond between the 14-amino group and the acetal oxygen is formed, resulting in the boat form-type conformation of the C ring. The calculations suggest that acetic anhydride reacts with the lone pair of the 17-amine above the D ring to generate an acylium salt 9 , whereas acetylation of the free form 1 proceeds on the primary amine at position 14 to produce 2 …”

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confidence: 99%

Unexpected Rearrangement Reactions of the 14-Aminonaltrexone Skeleton

et al. 2023

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The reaction of 14-aminonaltrexone with acetic anhydride was found to produce a range of different novel compounds between the free compound and its hydrochloride. The hydrochloride produced a compound with an acetylacetone moiety, whereas the free form produced a compound with a pyranopyridine moiety. Efforts to isolate reaction intermediates and density functional theory calculations have elucidated those formation mechanisms with both bearing the novel morphinan-type skeleton. Furthermore, a derivative with the acetylacetone moiety showed binding to opioid receptors.

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Green synthesis of a nano salt and its application as multifunctional organocatalyst for Knoevenagel condensation

Honarmand

2017

Res Chem Intermed

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Knoevenagel Condensation Reaction Using Ionic Liquid [ADPQ][CF3SO3] as Green and Reusable Catalyst

Cited by 4 publications

References 0 publications

Indole-Acrylonitrile Derivatives as Potential Antitumor and Antimicrobial Agents—Synthesis, In Vitro and In Silico Studies

Indole-Acrylonitrile Derivatives as Potential Antitumor and Antimicrobial Agents—Synthesis, In Vitro and In Silico Studies

Unexpected Rearrangement Reactions of the 14-Aminonaltrexone Skeleton

Green synthesis of a nano salt and its application as multifunctional organocatalyst for Knoevenagel condensation

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