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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,...

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Autores principales: Mehmood, Hina, Iqbal, Muhammad Asif, Ashiq, Muhammad Naeem, Hua, Ruimao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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.
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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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