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

Department of Chemistry

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

18 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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c8ob00624e

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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 = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2018.",

year = "2018",

doi = "10.1039/c8ob00624e",

language = "English",

volume = "16",

pages = "4482--4494",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "24",

}

TY - JOUR

T1 - Regioselective synthesis and biological evaluation of

T2 - N -substituted 2-aminoquinazolin-4-ones

AU - Liao, Zhen Yuan

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

PY - 2018

Y1 - 2018

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.

UR - http://www.scopus.com/inward/record.url?scp=85049049779&partnerID=8YFLogxK

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U2 - 10.1039/c8ob00624e

DO - 10.1039/c8ob00624e

M3 - Article

C2 - 29869668

AN - SCOPUS:85049049779

SN - 1477-0520

VL - 16

SP - 4482

EP - 4494

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

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

Abstract

ASJC Scopus subject areas

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CCDC 1821226: Experimental Crystal Structure Determination

CCDC 1821215: Experimental Crystal Structure Determination

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

Abstract

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Datasets

CCDC 1821226: Experimental Crystal Structure Determination

CCDC 1821215: Experimental Crystal Structure Determination

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