Synfacts 2005(1): 0115-0115  
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

Contributor(s): Victor Snieckus, Zhongdong Zhao
B. Cottineau, D. F. O’Shea*
University College Dublin, Ireland
Further Information

Publication History

Publication Date:
21 September 2005 (online)


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.