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

文献情報

出版日 2018-04-27

DOI 10.1039/C8OB00624E

インパクトファクター 3.876

著者

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

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要旨

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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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

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