Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2006(3): 0203-0203
DOI: 10.1055/s-2006-931970
DOI: 10.1055/s-2006-931970
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Regioselective Metallative Functionalization of 5-Azaindole
M. Lefoix, J.-P. Daillant, J.-Y. Mérour*, I. Gillaizeau, G. Coudert*
Université d’Orléans, France
Further Information
Publication History
Publication Date:
21 February 2006 (online)

Significance
The C-2- and C-3-controlled functionalization of 5-azaindoles using directed ortho-metallation (DoM) and metal-halogen exchange processes is reported. The choice of the directed metallation group (DMG) and the lithium base source were found to be crucial for the achievement of the observed results. Thus, using the N-benzenesulfonyl DMG allowed C-2 deprotonation with LDA and thereby the synthesis of various corresponding products such as halo derivatives, stannanes and boronic esters in good to excellent yields. On the other hand, electrophilic iodination followed by lithium-halogen exchange and electrophile quench led to similarly diverse C-3-substituted products in reasonable to excellent yields.