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Regioselective Synthesis and Biological Evaluation of N-substituted 2-aminoquinazolin-4-ones

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

Org Biomol Chem. 2018 Jun 20;16(24):4482-4494.

PMID: 29869668

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP555066	Aminobenzoate sodium		555-06-6	Price

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