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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Citations (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

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 journal › Article › peer-review

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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title = "Regioselective synthesis and biological evaluation of: N -substituted 2-aminoquinazolin-4-ones",

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.",

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

note = "Funding Information: This work was supported by Research Grants MOST 106-2113-M-003-006-and MOST 105-2113-M-003-003-from the Ministry of Science and Technology, Taiwan. We also thank Mr Ting-Shen Kuo (National Taiwan Normal University) for his assistance with X-ray crystallographic analysis. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2018.",

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AU - Yeh, Wen Hsiung

AU - Liao, Pen Yuan

AU - Liu, Yu Ting

AU - Chen, Ying Cheng

AU - Chen, Yi Hung

AU - Hsieh, Tsung Han

AU - Lin, Chia Chi

AU - Lu, Ming Hsuan

AU - Chen, Yi Song

AU - Hsu, Ming Chih

AU - Li, Tsai Kun

AU - Chien, Tun Cheng

N1 - Funding Information: This work was supported by Research Grants MOST 106-2113-M-003-006-and MOST 105-2113-M-003-003-from the Ministry of Science and Technology, Taiwan. We also thank Mr Ting-Shen Kuo (National Taiwan Normal University) for his assistance with X-ray crystallographic analysis. Publisher Copyright: © The Royal Society of Chemistry 2018.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 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.

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

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