Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones

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• 作者：Ting Li ; Minglu Chen ; Lei Yang ; Zhengxin Xiong ; Yongwei Wang ; Fei Li ; ^{kldlf@njmu.edu.cn" class="auth_mail" title="E-mail the corresponding author} ; Dongyin Chen ; ^{chendongyin321@163.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Copper ; Consecutive reaction ; 2-Halobenzamide ; Sodium azide ; Quinazolin-4(3H)-ones
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：11 February 2016
• 年：2016
• 卷：72
• 期：6
• 页码：868-874
• 全文大小：705 K

文摘

An efficient and practical copper-catalyzed consecutive synthesis of quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones from easily available 2-halobenzamides (or 2-halonicotinamides), aldehydes, and sodium azide has been developed, which gave the corresponding target products in 50–95% yields for 29 examples. This remarkable consecutive process involved sequential copper-catalyzed S_NAr, reduction, cyclization, and oxidation. Notably, this work would provide a novel synthetic strategy for bioactive molecules containing quinazolinone class skeletons.