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Org Biomol Chem. 2018 Jun 20;16(24):4482-4494. doi: 10.1039/c8ob00624e.

Regioselective synthesis and biological evaluation of N-substituted 2-aminoquinazolin-4-ones.

Author information

1
Department of Chemistry, National Taiwan Normal University, Taipei 116, Taiwan. tcchien@ntnu.edu.tw.

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.

PMID:
29869668
DOI:
10.1039/c8ob00624e
[Indexed for MEDLINE]

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