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

Zhen Yuan Liao, Wen Hsiung Yeh, Pen Yuan Liao, Yu Ting Liu, Ying Cheng Chen, Yi Hung Chen, Tsung Han Hsieh, Chia Chi Lin, Ming Hsuan Lu, Yi Song Chen, Ming Chih Hsu, Tsai Kun Li*, Tun Cheng Chien

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)4482-4494
Number of pages13
JournalOrganic and Biomolecular Chemistry
Issue number24
Publication statusPublished - 2018

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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