One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation

Ran Cheng; Tianjian Guo; Daisy Zhang-Negrerie; Yunfei Du; Kang Zhao

doi:10.1055/s-0033-1338521

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(21): 2998-3006
DOI: 10.1055/s-0033-1338521

paper

One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation

Ran Cheng

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Tianjian Guo

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Daisy Zhang-Negrerie

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Yunfei Du*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

,

Kang Zhao*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

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Abstract

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Abstract

A variety of 4(3H)-quinazolinones are synthesized conveniently in one pot from 2-aminobenzamides and aldehydes, via cyclization catalyzed by p-toluenesulfonic acid followed by oxidative dehydrogenation mediated by the hypervalent iodine compound phenyliodine diacetate [PhI(OAc)₂, PIDA]. Highlights of the described method include the first synthesis of quinazolinones bearing an N-alkoxy substituent, a new application of phenyliodine diacetate as an efficient dehydrogenative oxidant, and mild reaction conditions.

Key words

quinazolinones - cyclocondensation - dehydrogenation - phenyliodine diacetate - one-pot synthesis

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Referenzen

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