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Issue 24, 2018
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Regioselective synthesis and biological evaluation of N-substituted 2-aminoquinazolin-4-ones

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Abstract

The reaction of methyl anthranilates with N-arylcyanamides in the presence of p-TsOH in t-BuOH under reflux afforded predominantly 3-arylquinazolin-4-ones. In contrast, the reaction of the same reactants with TMSCl in t-BuOH at 60 °C followed by the Dimroth rearrangement in aqueous ethanolic sodium hydroxide gave exclusively the regioisomers, 2-(N-arylamino)quinazolin-4-ones. The regioselective synthesis of N-aryl-substituted 2-aminoquinazolin-4-ones can be further applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones.

Graphical abstract: Regioselective synthesis and biological evaluation of N-substituted 2-aminoquinazolin-4-ones

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Publication details

The article was received on 13 Mar 2018, accepted on 27 Apr 2018 and first published on 27 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00624E
Citation: Org. Biomol. Chem., 2018,16, 4482-4494
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    Regioselective synthesis and biological evaluation of N-substituted 2-aminoquinazolin-4-ones

    Z. Liao, W. Yeh, P. Liao, Y. Liu, Y. Chen, Y. Chen, T. Hsieh, C. Lin, M. Lu, Y. Chen, M. Hsu, T. Li and T. Chien, Org. Biomol. Chem., 2018, 16, 4482
    DOI: 10.1039/C8OB00624E

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