PubAg

Main content area

Palladium-Catalyzed Synthesis of 2,3-Disubstituted 5-Azaindoles via Heteroannulation Reaction and of 2-Substituted 5-Azaindoles through Domino Sila-Sonogashira/5-Endo Cyclization

Author:
Livecchi, Marion, Calvet, Géraldine, Schmidt, Frédéric
Source:
Journal of organic chemistry 2012 v.77 no.11 pp. 5006-5016
ISSN:
1520-6904
Subject:
catalytic activity, chemical reactions, chemical structure, organic chemistry, organic compounds, palladium, regioselectivity
Abstract:
A general and efficient procedure for the synthesis of 2,3-disubstituted 5-azaindoles through the palladium-catalyzed heteroannulation of 4-acetamido-3-iodopyridines and diaryl-, dialkyl-, or arylalkylalkynes is described along with a study of the reaction regioselectivity. The preparation of 2-monosubstituted 5-azaindoles via sila-Sonogashira/5-endo cyclization is also reported. These methods allowed us to prepare 36 diversely substituted 5-azaindoles in good yields.
Agid:
5498763