4.7 Article

Rh(III)-catalyzed redox-neutral annulation of azo and diazo compounds: one-step access to cinnolines

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 3, Issue 1, Pages 91-95

Publisher

CHINESE CHEMICAL SOC
DOI: 10.1039/c5qo00331h

Keywords

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Funding

  1. National Natural Science Foundation of China [NSFC21572272, NSFC21502232]
  2. Natural Science Foundation of Jiangsu Province [BK20140655, BK20130645]
  3. Foundation of State Key Laboratory of Natural Medicines [ZZJQ201306]

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Reported herein is a Rh-catalyzed redox-neutral annulation reaction between azo and diazo compounds, thus leading to the direct synthesis of cinnolines under mild conditions. The procedure exhibited a broad substrate scope, scalability and step economy, obviating the pre-functionalization of substrates and the use of oxidants. Further utilization of the resulting cinnolines provided efficient routes to some bioactive structures, such as 4-amino-cinnoline and 1-aminoindole.

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