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Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate
Hydroxy-cyanopyridines are easily synthesized via an advanced version of the Guareschi–Thorpe reaction by either three-component condensation of alkyl cyanoacetate or cyanoacetamide with 1,3-dicarbonyls and ammonium carbonate in an aqueous medium. Reactions proceed productively to give the desired p...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10440631/ https://www.ncbi.nlm.nih.gov/pubmed/37608967 http://dx.doi.org/10.1039/d3ra04590k |
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author | Tamaddon, Fatemeh Maddah-Roodan, Sajedeh |
author_facet | Tamaddon, Fatemeh Maddah-Roodan, Sajedeh |
author_sort | Tamaddon, Fatemeh |
collection | PubMed |
description | Hydroxy-cyanopyridines are easily synthesized via an advanced version of the Guareschi–Thorpe reaction by either three-component condensation of alkyl cyanoacetate or cyanoacetamide with 1,3-dicarbonyls and ammonium carbonate in an aqueous medium. Reactions proceed productively to give the desired products in high yields. Simple mechanistic monitoring showed the role of (NH(4))(2)CO(3) as both a nitrogen source for the pyridine ring and the reaction promoter. This new multicomponent approach for pyridine synthesis is inexpensive, user-friendly, and eco-friendly, while green buffer conditions, versatility, precipitation of products in the reaction medium, and simple work-up are extra advantages. |
format | Online Article Text |
id | pubmed-10440631 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-104406312023-08-22 Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate Tamaddon, Fatemeh Maddah-Roodan, Sajedeh RSC Adv Chemistry Hydroxy-cyanopyridines are easily synthesized via an advanced version of the Guareschi–Thorpe reaction by either three-component condensation of alkyl cyanoacetate or cyanoacetamide with 1,3-dicarbonyls and ammonium carbonate in an aqueous medium. Reactions proceed productively to give the desired products in high yields. Simple mechanistic monitoring showed the role of (NH(4))(2)CO(3) as both a nitrogen source for the pyridine ring and the reaction promoter. This new multicomponent approach for pyridine synthesis is inexpensive, user-friendly, and eco-friendly, while green buffer conditions, versatility, precipitation of products in the reaction medium, and simple work-up are extra advantages. The Royal Society of Chemistry 2023-08-21 /pmc/articles/PMC10440631/ /pubmed/37608967 http://dx.doi.org/10.1039/d3ra04590k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Tamaddon, Fatemeh Maddah-Roodan, Sajedeh Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate |
title | Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate |
title_full | Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate |
title_fullStr | Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate |
title_full_unstemmed | Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate |
title_short | Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate |
title_sort | advanced guareschi–thorpe synthesis of pyridines in green buffer, and ph-controlled aqueous medium with ammonium carbonate |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10440631/ https://www.ncbi.nlm.nih.gov/pubmed/37608967 http://dx.doi.org/10.1039/d3ra04590k |
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