Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of N‐Acyl Hydrazones with α‐Substituted Vinyl Azides

A palladium‐catalyzed cyclization of N‐acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α‐substituted vinyl azide serves as a...

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Veröffentlicht in:Advanced synthesis & catalysis 2020-03, Vol.362 (6), p.1362-1369
Hauptverfasser: Nie, Biao, Wu, Wanqing, Zeng, Wei, Ren, Qingyun, Zhang, Ji, Zhang, Yingjun, Jiang, Huanfeng
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Sprache:eng
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Zusammenfassung:A palladium‐catalyzed cyclization of N‐acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α‐substituted vinyl azide serves as an internal nitrogen source. Also, C−H bond activation and C−N bond cleavage have been realized using hydrazone as directing group.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901394