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Synfacts 2005(1): 0115-0115
DOI: 10.1055/s-2005-872209
DOI: 10.1055/s-2005-872209
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Carbolithiation of Vinyl Pyridines as a Route to 7-Azaindoles
B. Cottineau, D. F. O’Shea*
University College Dublin, Ireland
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. September 2005 (online)
Significance
This paper provides a new and efficient synthetic route to functionalized 7-azaindoles. The Suzuki carbolithiation/intramolecular Madelung-type sequence leads to indoles with R2 = n,- s-, t-Bu and R3 = Ph, t-Bu, C4H3S groups with little variation at R1 = H, Me substitution. It is a considerable improvement over several other methods for the synthesis of 2,3-substituted indoles such as Fischer indole and Madelung reactions.