Synthesis of Substituted Indole from 2-Aminobenzaldehyde through [1,2]-Aryl Shift
Patrick Levesque and Pierre-André Fournier
*Merck Frosst Center for Therapeutic Research, 16711 Trans
Canada Highway, Kirkland, Qc, Canada, H9H 3L1, Email: pierreandrefournier
gmail.com
P. Levesque, P.-A. Forunier, J. Org. Chem., 2010, 75, 7033-7036.
DOI: 10.1021/jo1016713
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Abstract
Addition of ethyl diazoacetate (EDA) to 2-aminobenzaldehydes cleanly affords 3-ethoxycarbonylindoles. This mild and efficient synthesis of indoles displays both excellent functional group tolerance and perfect regiochemical control. Various indole building blocks were synthesized from 2-aminobenzaldehydes derived from readily available anthranilic acids.
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Key Words
ID: J42-Y2010-2870
