Organic Chemistry Portal

Abstracts

Search:

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

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.

see article for more examples



Key Words

Indoles


ID: J42-Y2010-2870