Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source
In the presence of Cs<sub>2</sub>CO<sub>3</sub>, 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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/21/6599 |
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| author | Hina Mehmood Muhammad Asif Iqbal Muhammad Naeem Ashiq Ruimao Hua |
| author_facet | Hina Mehmood Muhammad Asif Iqbal Muhammad Naeem Ashiq Ruimao Hua |
| author_sort | Hina Mehmood |
| collection | DOAJ |
| description | In the presence of Cs<sub>2</sub>CO<sub>3</sub>, 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. |
| first_indexed | 2024-03-10T05:56:23Z |
| format | Article |
| id | doaj.art-fd414f594fda4315b0c92013718529d2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:56:23Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-fd414f594fda4315b0c92013718529d22023-11-22T21:23:44ZengMDPI AGMolecules1420-30492021-10-012621659910.3390/molecules26216599Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen SourceHina Mehmood0Muhammad Asif Iqbal1Muhammad Naeem Ashiq2Ruimao Hua3Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, ChinaKey Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, ChinaInstitute of Chemical Sciences, Bahauddin Zakariya University, Multan 608000, PakistanKey Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, ChinaIn the presence of Cs<sub>2</sub>CO<sub>3</sub>, 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.https://www.mdpi.com/1420-3049/26/21/6599base-promotedalkyne annulationpyridine derivativesbenzamide as nitrogen source |
| spellingShingle | Hina Mehmood Muhammad Asif Iqbal Muhammad Naeem Ashiq Ruimao Hua Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source Molecules base-promoted alkyne annulation pyridine derivatives benzamide 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 | base-promoted alkyne annulation pyridine derivatives benzamide as nitrogen source |
| url | https://www.mdpi.com/1420-3049/26/21/6599 |
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