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

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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.

Original languageEnglish
Pages (from-to)4482-4494
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number24
DOIs
Publication statusPublished - 2018 Jan 1

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ortho-Aminobenzoates
Sodium Hydroxide
sodium hydroxides
evaluation
synthesis
4-hydroxyquinazoline

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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Regioselective synthesis and biological evaluation of : N -substituted 2-aminoquinazolin-4-ones. / Liao, Zhen Yuan; Yeh, Wen Hsiung; Liao, Pen Yuan; Liu, Yu Ting; Chen, Ying Cheng; Chen, Yi Hung; Hsieh, Tsung Han; Lin, Chia Chi; Lu, Ming Hsuan; Chen, Yi Song; Hsu, Ming Chih; Li, Tsai Kun; Chien, Tun Cheng.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 24, 01.01.2018, p. 4482-4494.

Research output: Contribution to journalArticle

Liao, ZY, Yeh, WH, Liao, PY, Liu, YT, Chen, YC, Chen, YH, Hsieh, TH, Lin, CC, Lu, MH, Chen, YS, Hsu, MC, Li, TK & Chien, TC 2018, 'Regioselective synthesis and biological evaluation of: N -substituted 2-aminoquinazolin-4-ones', Organic and Biomolecular Chemistry, vol. 16, no. 24, pp. 4482-4494. https://doi.org/10.1039/c8ob00624e
Liao, Zhen Yuan ; Yeh, Wen Hsiung ; Liao, Pen Yuan ; Liu, Yu Ting ; Chen, Ying Cheng ; Chen, Yi Hung ; Hsieh, Tsung Han ; Lin, Chia Chi ; Lu, Ming Hsuan ; Chen, Yi Song ; Hsu, Ming Chih ; Li, Tsai Kun ; Chien, Tun Cheng. / Regioselective synthesis and biological evaluation of : N -substituted 2-aminoquinazolin-4-ones. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 24. pp. 4482-4494.
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