Get access

Copper-Catalyzed Aerobic Dehydrogenative Cyclization of N-Methyl-N-phenylhydrazones: Synthesis of Cinnolines

Authors

  • Dr. Guangwu Zhang,

    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
    Search for more papers by this author
  • Jinmin Miao,

    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
    Search for more papers by this author
  • Yan Zhao,

    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
    Search for more papers by this author
  • Prof. Dr. Haibo Ge

    Corresponding author
    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
    • Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
    Search for more papers by this author

  • We gratefully acknowledge Indiana University Purdue University Indianapolis for financial support. The Bruker 500 MHz NMR was purchased using funds from an NSF-MRI award (CHE-0619254).

Abstract

original image

O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a Cmath image[BOND]H bond functionalization process (see scheme; DMF=N,N′-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives.

Ancillary