A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry

Lakhinath Saikia,Ashim Jyoti Thakur,Jejiron Maheswari Baruah

doi:10.1186/2191-2858-1-12

Lakhinath Saikia, Ashim Jyoti Thakur + Show 1 more

Open Access

https://doi.org/10.1186/2191-2858-1-12

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Abstract

BackgroundSynthesis of oximes is an important reaction in organic chemistry, because these versatile oximes are used for protection, purification, and characterization of carbonyl compounds. Nitriles, amides via Beckmann rearrangement, nitro compounds, nitrones, amines, and azaheterocycles can be synthesised from oximes. They also find applications for selective α-activation. In inorganic chemistry, oximes act as a versatile ligand.Several procedures for the preparation of oximes exist, but, most of them have not addressed the green chemistry issue. They are associated with generation of pollutants, requirement of high reaction temperature, low yields, lack of a generalized procedure, etc. Hence, there is a demand for developing an efficient, convenient, and non-polluting or less polluting alternative method for the preparation of oximes. In this context, bismuth compounds are very useful as they are cheap in general, commercially available, air stable crystalline solids, safe, and non-toxic, hence easy to handle.ResultsCarbonyl compounds (aliphatic, heterocyclic, and aromatic) were converted into the corresponding oximes in excellent yields by simply grinding the reactants at room temperature without using any solvent in the presence of Bi2O3. Most importantly, this method minimizes waste disposal problems, provides a simple yet efficient example of unconventional methodology and requires short time.ConclusionsWe have developed a novel, quick, environmentally safe, and clean synthesis of aldoximes and ketoximes under solvent-free grinding condition.

Highlights

Synthesis of oximes is an important reaction in organic chemistry, because these versatile oximes are used for protection, purification, and characterization of carbonyl compounds
Oximes are highly crystalline compounds that find applications for protection, and for purification and characterization of carbonyl compounds [1,2].Conversions into nitriles [3], nitro compounds [4,5], nitrones [6], amines [7], and synthesis of azaheterocycles [8] are some of the synthetic applications of oximes
In continuation to our interest in protection and deprotection chemistry [29,30], we have developed a novel, quick, environmentally safe, and clean synthesis of aldoximes and ketoximes under grinding condition (Scheme 1) utilizing pestle and mortar under solventfree condition

Summary

Introduction

Synthesis of oximes is an important reaction in organic chemistry, because these versatile oximes are used for protection, purification, and characterization of carbonyl compounds. Oximes are highly crystalline compounds that find applications for protection, and for purification and characterization of carbonyl compounds [1,2].Conversions into nitriles [3], nitro compounds [4,5], nitrones [6], amines [7], and synthesis of azaheterocycles [8] are some of the synthetic applications of oximes They are useful for selective a-activation [9] and are extensively used as intermediates for the preparation of amides by the Beckmann rearrangement [10,11] and fungicides and herbicides [12]. Most bismuth (III) compounds have an LD50 value which is comparable to or even less than that of NaCl [28]

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