Synthesis of tricyclic ring systems: [2+2] ketene addition reaction for preparation of tricyclic ketone, alcohol, and lactone derivatives

Yılmaz, Özgür; Bekfelavi, Esen Yıldız; Kuş, Nermin Şimşek; Tunç, Tuncay; Şahin, Ertan

doi:10.1007/s11696-016-0013-7

Cited by 9 publications

(8 citation statements)

References 34 publications

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“…When the 1 H‐NMR spectra of synthesized molecules were examined, the signals of the NCH protons appear as singlet in the region between δ 8.85 and 7.77 ppm, which was also confirmed by the literature 32 . While the aromatic protons resonate at δ 6.84–8.08 ppm, 32 the double bond protons resonate at δ 5.23–6.73 ppm 42 . The CH and NCH 2 protons appear at δ 2.06–2.27 and δ 3.57–4.01 ppm, respectively.…”

Section: Resultssupporting

confidence: 66%

“…38,39 Then, 10 g (85.3 mmol) of nitrile 3 was dissolved in 100 mL ether and added dropwise at 0 C to slurry of 6.48 g (170.7 mmol) LiAlH 4 in 150 ml of ether. 42 The mixture was stirred 2 hr. After the starting compound finished according to TLC analysis, 30 ml of water and 10 ml of 20% NaOH solution were added slowly in the reaction mixture and stirred for 10 more minutes.…”

Section: Methodsmentioning

confidence: 99%

“…In the beginning the nitrile 3 was synthesized according to the literature 38,39 . Then, 10 g (85.3 mmol) of nitrile 3 was dissolved in 100 mL ether and added dropwise at 0°C to slurry of 6.48 g (170.7 mmol) LiAlH 4 in 150 ml of ether 42 . The mixture was stirred 2 hr.…”

Section: Methodsmentioning

confidence: 99%

“…32 While the aromatic protons resonate at δ 6.84-8.08 ppm, 32 the double bond protons resonate at δ 5.23-6.73 ppm. 42 The CH and NCH 2 protons appear at δ 2.06-2.27 and δ 3.57-4.01 ppm, respectively. In addition, the OCH 3 protons in the molecule 8d, resonate at δ 3.92 ppm.…”

mentioning

confidence: 98%

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Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Yılmaz

2021

J Chinese Chemical Soc

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New series of Schiff bases have been synthesized from the reaction between cyclohepta-2,4,6-trien-1-ylmethanamine and different aldehydes, and characterized via using 1 H NMR, 13 C NMR, FTIR spectroscopy, and GC-MS. After the successful synthesis, the in situ catalytic activity of all Schiff bases have been examined for the Suzuki C C cross-coupling reactions using phenylboronic acid, aryl bromides, and PdCl 2 as a catalyst. Before starting these investigations, reaction conditions were optimized using different bases and solvents. At the end of these reactions, the best efficiency was obtained in Et 3 N and EtOH. In addition to catalytic investigations, antioxidant activities of all synthesized Schiff bases were examined using DPPH and Iron (Fe 2+ ) chelation methods, and IC 50 values were calculated. While many molecules show various amounts of antioxidant activity, especially molecules 8e and 8g showed the best activity compared to butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA), which were used as positive controls, in DPPH and Iron chelating methods, respectively.

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Section: Resultssupporting

confidence: 66%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 98%

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Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Yılmaz

2021

J Chinese Chemical Soc

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“…Ketene addition reactions are one of the used methods in the synthesis of cyclobutanon (Snider 1988; Sengül et al 2000; Kishali et al 2011;Yılmaz et al 2017; Krepski and Hassner 1978). Cyclobutanones are valuable synthetic intermediates that participate in a variety of new and useful synthetic transformations.…”

Section: Introductionmentioning

confidence: 99%

Sonochemistry in organic synthesis: A convenient method for the preparation of halo-bicyclic molecules with keten addition reaction and biological properties of Dimethyl 7,7-dichloro-8-oxabicyclo[4.2.0]oct-3-ene-3,4- dicarboxylate

Sezen

Kuş

Özdemir

et al. 2022

Preprint

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A convenient method for the preparation of halo-bicyclic molecules likely to show biological activity, from keten addition reaction with dimethyl cyclohexa-1,4-diene-1,2-dicarboxylate (3) and dichloroketene, respectively, under ultrasound irradiation, is reported. First, 1,4-diene 3 had been synthesized with Diels-Alder addition, and then the ketene addition reaction was carried out. Ultrasonic and non-ultrasonic conditions in the ketene addition reaction were investigated. Then, lactones (8 and 9) were obtained from ketene adducts. The structures of the molecules were illuminated by IR, and NMR spectroscopy techniques, especially Cosy spectroscopy. The test compounds improved antioxidant ability from 9.48% to 69.29% at concentration rates of 12.5-200 mg/L. The newly synthesized dichloro lactone 8 showed good antibacterial activity against gram-negative and –positive bacteria and also, antifungal activity. The antibiofilm activity of dichloro lactone 8 investigated and it showed 99.92 and 99.14% biofilm inhibiton activity againts Staphylococcus aureus and Pseudomonas aeruginosa, respectively at concentration of 250 mg/L. Moreover, it was displayed 100% Escherichia coli viability inhibition at concentrations of 125 and 250 mg/L.

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Synthesis of Schiff Bases and Secondary Amines with Indane Skeleton; Evaluation of Their Antioxidant, Antibiotic, and Antifungal Activities

Erdoğan

Yılmaz

Çevik

et al. 2023

Chemistry & Biodiversity

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In this study, Schiff bases were synthesized by utilizing the reaction of 4‐ and 5‐aminoindane with substituted benzaldehydes. After the reduction of isolated Schiff bases with NaBH4, the corresponding secondary amine derivatives were obtained. The structures of all synthesized molecules were confirmed by 1H‐NMR, 13C‐NMR, FTIR, and ESI‐MS. Antioxidant activities of all synthesized molecules were investigated by DPPH method, and IC50 values were calculated. In addition, antibacterial activities of targets were investigated by the well diffusion method, and then MIC99 values were calculated. While only four of the sixteen synthesized molecules showed a high level of antioxidant activity, all of the molecules exhibited biological activity against gram‐positive and gram‐negative bacteria to varying degrees. In addition, all the synthesized molecules showed high antifungal activity. In antioxidant capacity studies, the IC50 values of 2‐(((2,3‐dihydro‐1H‐inden‐5‐yl)amino)methyl)‐6‐methoxyphenol (4d) and 2‐(((2,3‐dihydro‐1H‐inden‐4‐yl)amino)methyl)‐6‐methoxyphenol (7d) were determined to be 18.1 µg and 35.1 µg, respectively, and these values are much stronger than BHT (butylated hydroxytoluene) and BHA (butylated hydroxyanisole) used as positive controls. The fact that targets have the same core structure with different substituents has revealed a good structure‐activity relationship.

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Synthesis of tricyclic ring systems: [2+2] ketene addition reaction for preparation of tricyclic ketone, alcohol, and lactone derivatives

Cited by 9 publications

References 34 publications

Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Sonochemistry in organic synthesis: A convenient method for the preparation of halo-bicyclic molecules with keten addition reaction and biological properties of Dimethyl 7,7-dichloro-8-oxabicyclo[4.2.0]oct-3-ene-3,4- dicarboxylate

Synthesis of Schiff Bases and Secondary Amines with Indane Skeleton; Evaluation of Their Antioxidant, Antibiotic, and Antifungal Activities

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