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

doi:10.1039/c8ob00624e

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

Research output: Contribution to journal › Article

1 Citation (Scopus)

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 language	English
Pages (from-to)	4482-4494
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	24
DOIs	https://doi.org/10.1039/c8ob00624e
Publication status	Published - 2018 Jan 1

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Liao, Z. Y., Yeh, W. H., Liao, P. Y., Liu, Y. T., Chen, Y. C., Chen, Y. H., Hsieh, T. H., Lin, C. C., Lu, M. H., Chen, Y. S., Hsu, M. C., Li, T. K., & Chien, T. C. (2018). Regioselective synthesis and biological evaluation of: N -substituted 2-aminoquinazolin-4-ones. Organic and Biomolecular Chemistry, 16(24), 4482-4494. https://doi.org/10.1039/c8ob00624e

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 journal › Article

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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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.",

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AU - Liu, Yu Ting

AU - Chen, Ying Cheng

AU - Chen, Yi Hung

AU - Hsieh, Tsung Han

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AU - Li, Tsai Kun

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AB - 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.

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10.1039/c8ob00624e