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Tunable synthesis of quinolinone-fused isoquinolines through sequential one-pot nucleophilic addition and palladium-catalyzed intramolecular C–H alkenylation

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Abstract

An efficient sequential one-pot synthesis of fused heterocycles based on 4-quinolinone and isoquinoline scaffolds of biological interest has been developed. In all cases, the first nucleophilic addition of 2-aryl quinolin-4(1H)-ones to alkynyl bromides in tert-pentyl alcohol can proceed in a chemo-, regio- and stereoselective manner to give (Z)-N-(1-bromo-1-alken-2-yl)quinolin-4-ones at 110 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular aromatic C–H alkenylation in the presence of PdCl2 (5 mol%) in mixed solvents (tert-pentyl alcohol/DMF = 1 : 1), affording the novel quinolinone-fused isoquinoline derivatives in good yields.

Graphical abstract: Tunable synthesis of quinolinone-fused isoquinolines through sequential one-pot nucleophilic addition and palladium-catalyzed intramolecular C–H alkenylation

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Publication details

The article was received on 30 Sep 2018, accepted on 05 Dec 2018 and first published on 06 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02437E
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Tunable synthesis of quinolinone-fused isoquinolines through sequential one-pot nucleophilic addition and palladium-catalyzed intramolecular C–H alkenylation

    X. Li, Y. Bian, X. Chen, H. Zhang, W. Wang, S. Ren, X. Yang, C. Lu, C. Chen and J. Peng, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02437E

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