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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...

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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
Descripción
Sumario: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.