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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*

*Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Email: duyunfeiertju.edu.cn, kangzhaotju.edu.cn

R. Cheng, T. Guo, D. Zhang-Negrerie, Y. Du, K. Zhao, Synthesis, 2013, 45, 2998-3006.

DOI: 10.1055/s-0033-1338521 (free Supporting Information)


Abstract

Cyclization of 2-aminobenzamides and aldehydes catalyzed by p-toluenesulfonic acid followed by an efficient PIDA-mediated oxidative dehydrogenation enables the synthesis of various 4(3H)-quinazolinones - including quinazolinones bearing an N-alkoxy substituent. The method offers mild reaction conditions.

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Key Words

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


ID: J66-Y2013