Manganese(II)‐Mediated Domino Annulation Reaction of Vinyl Azides and 4‐Hydroxycoumarin: A Stereoselective Synthesis of Spirobenzofuranone‐lactams. Issue 19 (12th September 2016)

• Record Type: Journal Article
• Authors: Guo, Shanshan; Chen, Binhui; Zhao, Donghong; Chen, Wenteng; Zhang, Guolin
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 19(2016)
• Page Start: 3010
• Page End: 3014
• Publication Date: 2016-09-12
• Subjects: azides -- homogeneous catalysis -- 4-hydroxycoumarin -- manganese -- spiro compounds; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600423
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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 :