Manganese(II)-Mediated Domino Annulation Reaction of Vinyl Azides and 4-Hydroxycoumarin: A Stereoselective Synthesis of Spirobenzofuranone-lactams.
- Resource Type
- Article
- Authors
- Guo, Shanshan; Chen, Binhui; Zhao, Donghong; Chen, Wenteng; Zhang, Guolin
- Source
- Advanced Synthesis & Catalysis. 10/6/2016, Vol. 358 Issue 19, p3010-3014. 5p.
- Subject
- *CHEMICAL synthesis
*MANGANESE compounds
*MOLECULAR structure of manganese compounds
*CHEMICAL reactions
*ANNULATION
*STEREOSELECTIVE reactions
- Language
- ISSN
- 1615-4150
A manganese(II) acetate-catalyzed domino reaction of vinyl azides and 4-hydroxycoumarin has been developed for the synthesis of polyfunctionalized spirofuranone-lactams. A wide range of vinyl azides are capable of providing the desired spirofuranone-lactams in good to excellent yields. The reaction was achieved via thermal decomposition of vinyl azides to 2 H-azirines, followed by an intramolecular nucleophilic attack and stereoselective cyclization. The mild reaction conditions and easy operation make this reaction advantageous for the synthesis of spirofuranone-lactams. [ABSTRACT FROM AUTHOR]