Synthesis of New 3-Cyanocoumarins with C-6 Azo Function Using Ultrasound and Grinding Techniques in the Presence of Nano Fe&lt;sub&gt;3&lt;/sub&gt;O&lt;sub&gt;4&lt;/sub&gt;

Nikpassand, Mohammad; Fekri, Leila Zare; Changiz, Narjes; Imani, Forouzan

doi:10.2174/157017861101140113160517

Cited by 8 publications

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“…Mechanochemical heterocyclic chemistry (MHC) has recently attracted considerable interest from heterocyclic chemists, who have used this technique to achieve the green synthesis of several heterocyclic systems, including pyrazolines [8], aurones [9], bis(indol-3-yl)methanes [10], 1,3,4-oxadiazoles [11], pyrimidones [12], coumarins [13, 14], flavones [14], benzodiazepines [15], 1,6-naphthyridin [16] and 1,3,4-thiadiazoles [17]. Pravin and co-workers compared the mechanochemical synthesis of pyrazolyl chalcones with a conventional synthetic method.…”

Section: Introductionmentioning

confidence: 99%

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

Fahmy

El‐Sayed

Hemdan

2016

Chemistry Central Journal

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BackgroundMechano heterocyclic chemistry (MCH) is a recent quickly growing technique in the synthesis of heterocycles and draws the attention of heterocyclic chemists towards the uses of grindstone technique in a solvent free green efficient synthesis of many heterocyclic systems. On the other hand, multicomponent approach has opened the door for the rapid and efficient one-step procedures to synthesize a wide range of complex targets. Azlactones have been reported to exhibit a wide range of pharmaceutical properties including immune suppressive, anticancer. Antimicrobial, antitumor, anti-inflammatory and antiviral. It also used as useful synthons in the synthesis of several small molecules, including amino acids and peptides.ResultsThe present work describes an efficient one step green synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) via the multi-component synthesis by the mechanochemical grinding of glycine, benzoyl chloride, an aromatic aldehyde and fused sodium acetate in the presence of drops of acetic anhydride. This process is green, simple to handle, step and atom efficient, economical and environmentally friendly, because it does not require a reaction solvent or heating, we introduced the yield economy [YE] as a metric to assess the conversion efficiency of grinding and conventional synthetic reactions of azlactones. The structures of the newly synthesized compounds were elucidated by elemental and spectral analyses.ConclusionIn conclusion, we have developed a simple, efficient and eco-friendly strategy for facile synthesis of azlactones. The key advantages of this strategy, over conventional approach, include its simple, solvent free conditions, as well as its facile work-up, high yield economy and environmental friendliness. It is also successful in achieving three of the green chemistry objectives of a solvent free operation, high atom economy and step efficient. Thus, combining the features of both economic and environmental advantages.Graphical abstractAn efficient one step green synthesis of azlactones via multicomponent synthesis by a mechanochemical grinding.

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Section: Introductionmentioning

confidence: 99%

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

Fahmy

El‐Sayed

Hemdan

2016

Chemistry Central Journal

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ChemInform Abstract: Synthesis of New 3‐Cyanocoumarins with C‐6 Azo Function Using Ultrasound and Grinding Techniques in the Presence of Nano Fe₃O₄.

et al. 2014

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3O4. -Several substituted C-6 azo-functionalized 3-cyanocoumarins are either synthesized from azo aldehydes and malononitrile in the presence of reusable magnetic nano Fe 3O4 or by diazotization of 3-cyanocoumarins. The influence of ultrasound irradiation and grinding on the reaction yield is investigated. -(NIKPASSAND*, M.; FEKRI, L.; CHANGIZ, N.; IMANI, F.; Lett. Org. Chem. 11 (2014) 1, 29-34, http://dx.doi.org/10.2174/157017861101140113160517 ; Dep. Chem., Islamic Azad Univ., Rasht, Iran; Eng.) -F. Berndt 24-153

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Efficient Green Synthesis and Computational Chemical Study of Some Interesting Heterocyclic Derivatives as Insecticidal Agents

Fahmy

Rizk

Hemdan

et al. 2018

Journal of Heterocyclic Chem

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A series of 5,5‐diarylhydantoin (Dilantin) 3, 4, and 7, imidazole 1, 2, 5, 6, 8, and 9, thiazole 10–12, triazinthione 13, 15, 16, and 17, and thiadiazine 14 derivatives, containing diverse hydrophobic groups, were green synthesized through one‐pot stepwise reaction of aromatic aldehydes, vitamin B1, and nitrogen nucleophiles, for example, urea, thiourea, and thiosemicarbazide using grinding technique as well as conventional thermal methods. Such synthesized compounds have potent insecticidal activities; for example, compounds 4, 6, and 17 exhibited the highest insecticidal activity against both Plutella xylostella and Helicoverpa armigera with minimum inhibitory concentration values at 500 μg/mL and LD50 activities at 50 μg/mL. The density functional theory was then applied to explore the structural and electronic characteristics of these compounds. All the synthesized compounds have been characterized based on their elemental analyses and spectral data.

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Synthesis of New 3-Cyanocoumarins with C-6 Azo Function Using Ultrasound and Grinding Techniques in the Presence of Nano Fe<sub>3</sub>O<sub>4</sub>

Cited by 8 publications

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Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

ChemInform Abstract: Synthesis of New 3‐Cyanocoumarins with C‐6 Azo Function Using Ultrasound and Grinding Techniques in the Presence of Nano Fe₃O₄.

Efficient Green Synthesis and Computational Chemical Study of Some Interesting Heterocyclic Derivatives as Insecticidal Agents

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Synthesis of New 3-Cyanocoumarins with C-6 Azo Function Using Ultrasound and Grinding Techniques in the Presence of Nano Fe<sub>3</sub>O<sub>4</sub>

Cited by 8 publications

References 0 publications

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

ChemInform Abstract: Synthesis of New 3‐Cyanocoumarins with C‐6 Azo Function Using Ultrasound and Grinding Techniques in the Presence of Nano Fe3O4.

Efficient Green Synthesis and Computational Chemical Study of Some Interesting Heterocyclic Derivatives as Insecticidal Agents

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ChemInform Abstract: Synthesis of New 3‐Cyanocoumarins with C‐6 Azo Function Using Ultrasound and Grinding Techniques in the Presence of Nano Fe₃O₄.