Abstract
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.
Highlights
Mechano heterocyclic chemistry (MCH) is a recent quickly growing technique in the synthesis of het‐ erocycles and draws the attention of heterocyclic chemists towards the uses of grindstone technique in a solvent free green efficient synthesis of many heterocyclic systems
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]
Based on the many benefits reported for MHC, we envisaged that this approach could be used to provide facile access to azlactones as a greener, more efficient and yield-economic strategy compared with conventional methods
Summary
Mechano heterocyclic chemistry (MCH) is a recent quickly growing technique in the synthesis of het‐ erocycles and draws the attention of heterocyclic chemists towards the uses of grindstone technique in a solvent free green efficient synthesis of many heterocyclic systems. Fahmy et al Chemistry Central Journal (2016) 10:59 together of the crystals of two different reagents in a pestle and mortar leads to the formation of local heat, which mediates a reaction between these two materials. These reactions are easy to handle and are generally considered to be more economical and environmentally friendly (i.e., greener) than conventional techniques. Pravin and co-workers compared the mechanochemical synthesis of pyrazolyl chalcones with a conventional synthetic method They found that the former of these two required shorter reaction times, afforded higher yields of the desired chalcone products and proceeded smoothly at room temperature [18]. Based on the many benefits reported for MHC, we envisaged that this approach could be used to provide facile access to azlactones as a greener, more efficient and yield-economic strategy compared with conventional methods
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