Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2, 3-d]pyrimidin-4(3H)-ones. Issue 6 (11th February 2016)

• Record Type: Journal Article
• Authors: Li, Ting; Chen, Minglu; Yang, Lei; Xiong, Zhengxin; Wang, Yongwei; Li, Fei; Chen, Dongyin
• Is Part Of: Tetrahedron. Volume 72:Issue 6(2016)
• Page Start: 868
• Page End: 874
• Publication Date: 2016-02-11
• Subjects: Copper -- Consecutive reaction -- 2-Halobenzamide -- Sodium azide -- Quinazolin-4(3H)-ones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.12.059
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient and practical copper-catalyzed consecutive synthesis of quinazolin-4(3 H )-ones and pyrido[2, 3- d ]pyrimidin-4(3 H )-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 SN Ar, reduction, cyclization, and oxidation. Notably, this work would provide a novel synthetic strategy for bioactive molecules containing quinazolinone class skeletons. Graphical abstract: