Synthesis of quinazolinones via radical cyclization of α-azidyl benzamides

被引：18

作者：

Yang, Tonghao ^{[1
]}

Wang, Weixia ^{[1
]}

Wei, Dian ^{[1
]}

Zhang, Tianqi ^{[1
]}

Han, Bing ^{[1
]}

Yu, Wei ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 03期

基金：

中国国家自然科学基金;

关键词：

CATALYZED CARBONYLATIVE SYNTHESIS; NITROGEN-CENTERED RADICALS; TERT-BUTYL HYDROPEROXIDE; C BOND-CLEAVAGE; VINYL AZIDES; 1,3-DICARBONYL COMPOUNDS; OXIDATIVE SYNTHESIS; O-AMINOBENZAMIDES; GLYCOSYL AZIDES; IMINYL RADICALS;

D O I：

10.1039/c6qo00656f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper reports a new radical-based method for the synthesis of quinazolinones from alpha-azidyl benzamides. Under the conditions of visible light irradiation with N-bromosuccinimide (NBS), alpha-azidyl benzamides were transformed into the corresponding iminyl radicals via regio-selective alpha-hydrogen abstraction and denitrogenation; the thus formed iminyl radicals then underwent cyclization to afford the quinazolinones. The scope of this method was examined by applying it to alpha-azidyl benzamides of different structural features. It was found that the key cyclization step is influenced by conformational effects as well as substituent effects. As the current approach can be implemented under mild tin-free conditions by using readily accessible precursors, it has practical applicability in the synthesis of quinazolinones.

引用

页码：421 / 426

页数：6

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