Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Understanding and Interrupting the Fischer Azaindolization Reaction

Understanding and Interrupting the Fischer Azaindolization Reaction
Bryan J. Simmons, Pier Alexandre Champagne, Neil K. Garg, Katsuya Yamakawa, Lucas A. Morrill, Elias Picazo, K. N. Houk, Marie Hoffmann
Experimental and computational studies pertaining to the Fischer azaindolization reaction are reported. These studies explain why pyridylhydrazines are poorly reactive in Fischer indolization reactions, in addition to the origin of hydrazine substituent effects. Additionally, an interrupted variant of Fischer azaindolization methodology is disclosed, which provides a synthetic entryway into fused azaindoline scaffolds.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07518

DOI: 10.1021/jacs.7b07518

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