An iodine-mediated green synthesis of 1,3,4-oxadiazoles under solvent-free conditions using grinding technique

Kumar, Ashish; Makrandi, J. K.

doi:10.1080/17518253.2010.502909

Cited by 15 publications

(7 citation statements)

References 11 publications

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“…However, good synthetic methods of 1,3,4‐oxadiazoles from hydrazide and aldehyde under totally solvent‐free conditions are not well known. Even though an iodine‐mediated synthesis of 1,3,4‐oxadiazoles under solvent‐free conditions using grinding technique has been reported recently, it was not reproduced in our laboratory …”

Section: Methodsmentioning

confidence: 98%

Highly Efficient One‐Pot Solvent‐Free Synthesis of 2,5‐Disubstituted‐1,3,4‐Oxadiazole via BTI‐mediated Oxidation of N‐Acylhydrazone from Hydrazide and Aldehyde

Yan

Lee

Noh

et al. 2017

Bulletin Korean Chem Soc

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Section: Methodsmentioning

confidence: 98%

Highly Efficient One‐Pot Solvent‐Free Synthesis of 2,5‐Disubstituted‐1,3,4‐Oxadiazole via BTI‐mediated Oxidation of N‐Acylhydrazone from Hydrazide and Aldehyde

Yan

Lee

Noh

et al. 2017

Bulletin Korean Chem Soc

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“…This was proven by 1 H NMR shifts for protons of the -COCH 3 group (1.21-2.30 ppm), as well as mass spectra where peaks of molecular ions were in accordance with acetylated compounds. Our attempt was to synthesize 1,3,4-oxadiazoles from Schiff bases employing other protocols too, like grinding Schiff bases with molecular iodine, 24 or cyclization with chloramine T 21 or ceric ammonium nitrate. 27 However, although some authors describe them as very effective procedures, they were not suitable for our type of compounds.…”

Section: Resultsmentioning

confidence: 99%

Biological study on novel coumarinyl 1,3,4-oxadiazoles

Molnar¹,

Amić²,

Pavić³

et al. 2018

Turk J Chem

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Coumarinyl 1,3,4-oxadiazoles were synthesized from Schiff bases and acetic anhydride. All compounds were characterized by melting points and their structures confirmed by mass and 1 H and 13 C NMR spectrometry.These novel coumarinyl derivatives were subjected to antibacterial, antifungal, antaflatoxigenic, and antioxidant activity.Their activity varied depending on their structure, where 2-(3-acetyl-5-(((4-methyl-2-oxo-2 H -chromen-7-yl)oxy)methyl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-1,4-phenylene diacetate showed significant antioxidant and antibacterial activity on B.subtilis. 4-(3-Acetyl-5-(((4-methyl-2-oxo-2 H -chromen-7-yl)oxy)methyl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-1,2-phenylene diacetate was found to possess excellent antifungal and antiaflatoxigenic activity.

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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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An iodine-mediated green synthesis of 1,3,4-oxadiazoles under solvent-free conditions using grinding technique

Cited by 15 publications

References 11 publications

Highly Efficient One‐Pot Solvent‐Free Synthesis of 2,5‐Disubstituted‐1,3,4‐Oxadiazole via BTI‐mediated Oxidation of N‐Acylhydrazone from Hydrazide and Aldehyde

Highly Efficient One‐Pot Solvent‐Free Synthesis of 2,5‐Disubstituted‐1,3,4‐Oxadiazole via BTI‐mediated Oxidation of N‐Acylhydrazone from Hydrazide and Aldehyde

Biological study on novel coumarinyl 1,3,4-oxadiazoles

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

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