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Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source
In the presence of Cs(2)CO(3), the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine derivatives accompanies the outcome of 1,...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587654/ https://www.ncbi.nlm.nih.gov/pubmed/34771009 http://dx.doi.org/10.3390/molecules26216599 |
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author | Mehmood, Hina Iqbal, Muhammad Asif Ashiq, Muhammad Naeem Hua, Ruimao |
author_facet | Mehmood, Hina Iqbal, Muhammad Asif Ashiq, Muhammad Naeem Hua, Ruimao |
author_sort | Mehmood, Hina |
collection | PubMed |
description | In the presence of Cs(2)CO(3), the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine derivatives accompanies the outcome of 1,3-diaryl propenes, which are also useful intermediates in organic synthesis. Thus, pyridine ring results from a formal [2+2+1+1] cyclocondensation of three alkynes with benzamides, and one of the alkynes provides one carbon, whilst benzamides provide a nitrogen source only. A new transformation of alkynes as well as new utility of benzamide are found in this work. |
format | Online Article Text |
id | pubmed-8587654 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-85876542021-11-13 Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source Mehmood, Hina Iqbal, Muhammad Asif Ashiq, Muhammad Naeem Hua, Ruimao Molecules Article In the presence of Cs(2)CO(3), the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine derivatives accompanies the outcome of 1,3-diaryl propenes, which are also useful intermediates in organic synthesis. Thus, pyridine ring results from a formal [2+2+1+1] cyclocondensation of three alkynes with benzamides, and one of the alkynes provides one carbon, whilst benzamides provide a nitrogen source only. A new transformation of alkynes as well as new utility of benzamide are found in this work. MDPI 2021-10-31 /pmc/articles/PMC8587654/ /pubmed/34771009 http://dx.doi.org/10.3390/molecules26216599 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Mehmood, Hina Iqbal, Muhammad Asif Ashiq, Muhammad Naeem Hua, Ruimao Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source |
title | Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source |
title_full | Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source |
title_fullStr | Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source |
title_full_unstemmed | Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source |
title_short | Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source |
title_sort | base-promoted one-pot synthesis of pyridine derivatives via aromatic alkyne annulation using benzamides as nitrogen source |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587654/ https://www.ncbi.nlm.nih.gov/pubmed/34771009 http://dx.doi.org/10.3390/molecules26216599 |
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