Substrate-Tuned Domino Annulation for Selective Synthesis of Poly-substituted Benzo[f]imidazo[2,1‑a][2,7]naphthyridines and 3‑Azaheterocyclic Substituted 2‑Arylquinolines
A domino annulation/oxidation of heterocyclic ketene aminals (HKAs) and 2-aminochalcones has been developed for the selective synthesis of poly-substituted benzo[f]imidazo[2,1-a][2,7]naphthyridines and 3-azaheterocyclic substituted 2-arylquinolines. These reactions proceed well under mild condi...
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Veröffentlicht in: | Journal of organic chemistry 2021-03, Vol.86 (6), p.4747-4755 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A domino annulation/oxidation of heterocyclic ketene aminals (HKAs) and 2-aminochalcones has been developed for the selective synthesis of poly-substituted benzo[f]imidazo[2,1-a][2,7]naphthyridines and 3-azaheterocyclic substituted 2-arylquinolines. These reactions proceed well under mild conditions without any additives. Plausible mechanisms for such a polycyclic ring system assembly were also proposed. Moreover, benzo[f]imidazo[2,1-a][2,7]naphthyridine 3g displayed a fluorescence effect, demonstrating the potential applications in organic optical materials. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.1c00112 |