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

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

18 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	4482-4494
頁數	13
期刊	Organic and Biomolecular Chemistry
卷	16
發行號	24
DOIs	https://doi.org/10.1039/c8ob00624e
出版狀態	已發佈 - 2018

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

存取文件

10.1039/c8ob00624e

其它文件與鏈接

Link to publication in Scopus

CCDC 1821226: Experimental Crystal Structure Determination
Liao, Z. (Creator), Yeh, W. (Creator), Liao, P. (Creator), Liu, Y. (Creator), Chen, Y. (Creator), Chen, Y. (Creator), Hsieh, T. (Creator), Lin, C. (Creator), Lu, M. (Creator), Chen, Y. (Creator), Hsu, M. (Creator), Li, T. (Creator) & Chien, T. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1z447h, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1z447h&sid=DataCite
資料集: Dataset
CCDC 1821215: Experimental Crystal Structure Determination
Liao, Z. (Creator), Yeh, W. (Creator), Liao, P. (Creator), Liu, Y. (Creator), Chen, Y. (Creator), Chen, Y. (Creator), Hsieh, T. (Creator), Lin, C. (Creator), Lu, M. (Creator), Chen, Y. (Creator), Hsu, M. (Creator), Li, T. (Creator) & Chien, T. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1z43w3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1z43w3&sid=DataCite
資料集: Dataset

引用此

@article{80f49a8f5cce4983b4c2f3a6261d2ce0,

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",

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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.

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

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1821226: Experimental Crystal Structure Determination

CCDC 1821215: Experimental Crystal Structure Determination

引用此