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A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry
BACKGROUND: Synthesis 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...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer
2011
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3339398/ https://www.ncbi.nlm.nih.gov/pubmed/22373136 http://dx.doi.org/10.1186/2191-2858-1-12 |
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author | Saikia, Lakhinath Baruah, Jejiron Maheswari Thakur, Ashim Jyoti |
author_facet | Saikia, Lakhinath Baruah, Jejiron Maheswari Thakur, Ashim Jyoti |
author_sort | Saikia, Lakhinath |
collection | PubMed |
description | BACKGROUND: Synthesis 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. RESULTS: Carbonyl 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 Bi(2)O(3). Most importantly, this method minimizes waste disposal problems, provides a simple yet efficient example of unconventional methodology and requires short time. CONCLUSIONS: We have developed a novel, quick, environmentally safe, and clean synthesis of aldoximes and ketoximes under solvent-free grinding condition. |
format | Online Article Text |
id | pubmed-3339398 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Springer |
record_format | MEDLINE/PubMed |
spelling | pubmed-33393982012-04-30 A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry Saikia, Lakhinath Baruah, Jejiron Maheswari Thakur, Ashim Jyoti Org Med Chem Lett Original BACKGROUND: Synthesis 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. RESULTS: Carbonyl 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 Bi(2)O(3). Most importantly, this method minimizes waste disposal problems, provides a simple yet efficient example of unconventional methodology and requires short time. CONCLUSIONS: We have developed a novel, quick, environmentally safe, and clean synthesis of aldoximes and ketoximes under solvent-free grinding condition. Springer 2011-10-04 /pmc/articles/PMC3339398/ /pubmed/22373136 http://dx.doi.org/10.1186/2191-2858-1-12 Text en Copyright © 2011 Saikia et al; licensee Springer. https://creativecommons.org/licenses/by/2.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0 (https://creativecommons.org/licenses/by/2.0/) ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Original Saikia, Lakhinath Baruah, Jejiron Maheswari Thakur, Ashim Jyoti A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry |
title | A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry |
title_full | A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry |
title_fullStr | A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry |
title_full_unstemmed | A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry |
title_short | A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry |
title_sort | rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry |
topic | Original |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3339398/ https://www.ncbi.nlm.nih.gov/pubmed/22373136 http://dx.doi.org/10.1186/2191-2858-1-12 |
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