Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Tamaddon, Fatemeh, Maddah-Roodan, Sajedeh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
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
_version_ 1785093202258165760
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
work_keys_str_mv AT tamaddonfatemeh advancedguareschithorpesynthesisofpyridinesingreenbufferandphcontrolledaqueousmediumwithammoniumcarbonate
AT maddahroodansajedeh advancedguareschithorpesynthesisofpyridinesingreenbufferandphcontrolledaqueousmediumwithammoniumcarbonate