Metal‐Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH 4 ) 2 S 2 O 8 ‐Promoted Intramolecular Oxidative Cyclization

Metal‐Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH 4 ) 2 S 2 O 8 ‐Promoted Intramolecular Oxidative Cyclization

An efficient metal‐free, (NH 4 ) 2 S 2 O 8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthri...

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Bibliographic Details
Published in:European journal of organic chemistry Vol. 2019; no. 22; pp. 3649 - 3653
Main Authors: Xie, Lijuan, Lu, Cong, Jing, Dong, Ou, Xinrui, Zheng, Ke
Format: Journal Article
Language:English
Published: 16-06-2019
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Summary:An efficient metal‐free, (NH 4 ) 2 S 2 O 8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon‐centered radical was involved in the catalytic cycle.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900469