摘要
We report on a copper-catalyzed three-component reaction for the synthesis of disubstituted nicotinonitriles using 3-bromopropenals, benzoylacetonitriles, and ammonium acetate (NH4OAc). The Knoevenagel-type condensation of 3-bromopropenals with benzoylacetonitriles gives δ-bromo-2,4-dienones that contain strategically placed functional groups that react with the ammonia generated in situ to give the corresponding azatrienes. These azatrienes can then be transformed into trisubstituted pyridines under the reaction conditions via a reaction sequence involving 6π-azaelectrocyclization and aromatization.
原文 | 英語 |
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頁(從 - 到) | 10298-10305 |
頁數 | 8 |
期刊 | Journal of Organic Chemistry |
卷 | 88 |
發行號 | 14 |
DOIs | |
出版狀態 | 已發佈 - 2023 7月 21 |
ASJC Scopus subject areas
- 有機化學
指紋
深入研究「One-Pot Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Disubstituted Nicotinonitriles」主題。共同形成了獨特的指紋。資料集
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CCDC 2271339: Experimental Crystal Structure Determination
Lin, L. (Contributor), Suresh, S. (Contributor), Lin, K. (Contributor), Kavala, V. (Contributor) & Yao, C. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2g7j08, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2g7j08&sid=DataCite
資料集: Dataset