Copper‐Catalyzed N‐Arylation of Polysubstituted Pyridines Synthesized by the Novel Reaction of N‐Sulfonyl Ketenimine and Malononitrile‐Trichloroacetonitrile Adduct
In this study, we synthesized some new derivatives of N‐(4‐amino‐5‐cyano‐6‐(trichloromethyl)pyridin‐2‐yl)alkyl sulfonamides in the presence of a copper catalyst. A one‐pot reaction system was used, and four components participated in the process. These four components were sulfonyl azides, terminal...
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| Veröffentlicht in: | Journal of heterocyclic chemistry 2019-09, Vol.56 (9), p.2604-2611 |
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| container_issue | 9 |
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| container_title | Journal of heterocyclic chemistry |
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| creator | Nematpour, Manijeh Fasihi Dastjerdi, Hossein Mahboubi Rabbani, Sayyed Mohammad Ismaeil Tabatabai, Sayyed Abbas |
| description | In this study, we synthesized some new derivatives of N‐(4‐amino‐5‐cyano‐6‐(trichloromethyl)pyridin‐2‐yl)alkyl sulfonamides in the presence of a copper catalyst. A one‐pot reaction system was used, and four components participated in the process. These four components were sulfonyl azides, terminal alkynes, malononitrile, and trichloroacetonitrile. The reaction rate was increased by the use of copper (I) iodide as the catalyst and tetrahydrofuran was used as the solvent. We achieved the final compounds in moderate to good yields. Moreover, we converted “NH2” side group to N‐aryl by the use of various aryl halide analogs in acetonitrile as the solvent, under mild reaction and at the room temperature. |
| doi_str_mv | 10.1002/jhet.3668 |
| format | Article |
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| identifier | ISSN: 0022-152X |
| ispartof | Journal of heterocyclic chemistry, 2019-09, Vol.56 (9), p.2604-2611 |
| issn | 0022-152X 1943-5193 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Acetonitrile Alkynes Aromatic compounds Catalysis Catalysts Copper Iodides Malononitrile Pyridines Solvents Sulfonamides Tetrahydrofuran |
| title | Copper‐Catalyzed N‐Arylation of Polysubstituted Pyridines Synthesized by the Novel Reaction of N‐Sulfonyl Ketenimine and Malononitrile‐Trichloroacetonitrile Adduct |
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