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Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines

The synthesis of six-membered oxygen- and nitrogen-containing heterocycles has been regarded as the most fundamental issue in organic chemistry and the chemical industry because these heterocycles are used in producing high-value products. In this study, an efficient, economic, sustainable, and gree...

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Autores principales: Ghiai, Ramin, Alavinia, Sedigheh, Ghorbani-Vaghei, Ramin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9516894/
https://www.ncbi.nlm.nih.gov/pubmed/36320279
http://dx.doi.org/10.1039/d2ra05070f
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author Ghiai, Ramin
Alavinia, Sedigheh
Ghorbani-Vaghei, Ramin
author_facet Ghiai, Ramin
Alavinia, Sedigheh
Ghorbani-Vaghei, Ramin
author_sort Ghiai, Ramin
collection PubMed
description The synthesis of six-membered oxygen- and nitrogen-containing heterocycles has been regarded as the most fundamental issue in organic chemistry and the chemical industry because these heterocycles are used in producing high-value products. In this study, an efficient, economic, sustainable, and green protocol for their multicomponent synthesis has been developed. The one-pot direct Knoevenagel condensation–Michael addition–cyclization sequences for the transformation of aromatic aldehydes, malononitrile, and 2-aminopyridine generate the corresponding 1,8-naphthyridines over a novel mesoporous bifunctional organocatalyst supported cholorosulfonic acid [poly(triazine-benzene sulfonamide)-SO(3)H (PTBSA-SO(3)H)] under ambient conditions. The catalyst was used for the formation of 1,8-naphthyridine derivatives for six runs. The current strategy provided a wider substrate range, and short reaction times.
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spelling pubmed-95168942022-10-31 Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines Ghiai, Ramin Alavinia, Sedigheh Ghorbani-Vaghei, Ramin RSC Adv Chemistry The synthesis of six-membered oxygen- and nitrogen-containing heterocycles has been regarded as the most fundamental issue in organic chemistry and the chemical industry because these heterocycles are used in producing high-value products. In this study, an efficient, economic, sustainable, and green protocol for their multicomponent synthesis has been developed. The one-pot direct Knoevenagel condensation–Michael addition–cyclization sequences for the transformation of aromatic aldehydes, malononitrile, and 2-aminopyridine generate the corresponding 1,8-naphthyridines over a novel mesoporous bifunctional organocatalyst supported cholorosulfonic acid [poly(triazine-benzene sulfonamide)-SO(3)H (PTBSA-SO(3)H)] under ambient conditions. The catalyst was used for the formation of 1,8-naphthyridine derivatives for six runs. The current strategy provided a wider substrate range, and short reaction times. The Royal Society of Chemistry 2022-09-28 /pmc/articles/PMC9516894/ /pubmed/36320279 http://dx.doi.org/10.1039/d2ra05070f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Ghiai, Ramin
Alavinia, Sedigheh
Ghorbani-Vaghei, Ramin
Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines
title Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines
title_full Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines
title_fullStr Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines
title_full_unstemmed Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines
title_short Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines
title_sort chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9516894/
https://www.ncbi.nlm.nih.gov/pubmed/36320279
http://dx.doi.org/10.1039/d2ra05070f
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