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Copper-catalyzed cascade reaction: synthesis of pyrimido[4,5-b]quinolinones from 2-chloroquinoline-3-carbonitriles with (aryl)methanamines

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Abstract

Cu-catalyzed cascade reaction of 2-chloroquinoline-3-carbonitriles with benzyl amines and sodium hydroxide in aerobic atmosphere has been developed for the synthesis of pyrimido[4,5-b]quinoline-4-ones. The reaction proceeds sequentially via Ullmann-coupling and conversion of nitrile to amide followed by nucleophilic addition of amide nitrogen onto iminium carbon and air oxidation. Reagents and substrates are cheap and easily available/accessible. Plausible mechanism of reaction is also discussed.

Graphical abstract: Copper-catalyzed cascade reaction: synthesis of pyrimido[4,5-b]quinolinones from 2-chloroquinoline-3-carbonitriles with (aryl)methanamines

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Publication details

The article was received on 30 Nov 2017, accepted on 17 Jan 2018 and first published on 01 Feb 2018


Article type: Paper
DOI: 10.1039/C7NJ04689H
Citation: New J. Chem., 2018, Advance Article
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    Copper-catalyzed cascade reaction: synthesis of pyrimido[4,5-b]quinolinones from 2-chloroquinoline-3-carbonitriles with (aryl)methanamines

    J. B. Singh, K. Mishra, T. Gupta and R. M. Singh, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ04689H

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