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: pierreandrefourniergmail.com
P. Levesque, P.-A. Forunier, J. Org. Chem., 2010, 75, 7033-7036.
DOI: 10.1021/jo1016713 (free Supporting Information)
see article for more reactions
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.
see article for more examples