Rapid Synthesis of Highly Substituted 1,6-Naphthyridines Via Heteroaryl Ditriflates
We report the discovery of a convenient and efficient method for the synthesis of highly substituted 1,6-naphthyridines. A tandem nitrile hydration/cyclization procedure was developed to access 1,6-naphthyridine-5,7-diones under mild conditions. Subsequently, we have found that ditriflation of these...
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| Veröffentlicht in: | Journal of organic chemistry 2024-08, Vol.89 (15), p.10912-10918 |
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| container_end_page | 10918 |
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| container_issue | 15 |
| container_start_page | 10912 |
| container_title | Journal of organic chemistry |
| container_volume | 89 |
| creator | Shimkin, Kirk W. Compton, Jordan S. Diccianni, Justin B. Waldo, Jesse P. Jones, William M. Krawczuk, Paul J. Rosano, Robert J. |
| description | We report the discovery of a convenient and efficient method for the synthesis of highly substituted 1,6-naphthyridines. A tandem nitrile hydration/cyclization procedure was developed to access 1,6-naphthyridine-5,7-diones under mild conditions. Subsequently, we have found that ditriflation of these intermediates provides 1,6-naphthyridine-5,7-ditriflates which are bench-stable but highly reactive intermediates that can be engaged in one-pot difunctionalization reactions leading to diverse drug-like products in rapid fashion. |
| doi_str_mv | 10.1021/acs.joc.4c01248 |
| format | Article |
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| ispartof | Journal of organic chemistry, 2024-08, Vol.89 (15), p.10912-10918 |
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| language | eng |
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| source | ACS Journals: American Chemical Society Web Editions |
| subjects | heterocyclic compounds methodology organic chemistry |
| title | Rapid Synthesis of Highly Substituted 1,6-Naphthyridines Via Heteroaryl Ditriflates |
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