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
Hauptverfasser: Ying, Zhimin, Cen, Jie, Luo, Feng, Wu, You, Liu, Shuangrong, Chen, Wenteng, Shao, Jiaan, Yu, Yongping
Format: Artikel
Sprache:eng
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00112