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

25 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

Cite this

@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",

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 - https://www.scopus.com/pages/publications/85049049779

UR - https://www.scopus.com/pages/publications/85049049779#tab=citedBy

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 1821215: Experimental Crystal Structure Determination

CCDC 1821226: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1821215: Experimental Crystal Structure Determination

CCDC 1821226: Experimental Crystal Structure Determination

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