Synthesis of quinazolinones via radical cyclization of α-azidyl benzamides

文献情報

出版日 2016-12-16

DOI 10.1039/C6QO00656F

インパクトファクター 5.281

著者

Tonghao Yang, Weixia Wang, Dian Wei, Tianqi Zhang, Bing Han, Wei Yu

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要旨

This paper reports a new radical-based method for the synthesis of quinazolinones from α-azidyl benzamides. Under the conditions of visible light irradiation with N-bromosuccinimide (NBS), α-azidyl benzamides were transformed into the corresponding iminyl radicals via regio-selective α-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 α-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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Synthesis of quinazolinones via radical cyclization of α-azidyl benzamides

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