Synfacts 2005(1): 0116-0116  
DOI: 10.1055/s-2005-872210
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fused Indoles by Sequential Heck Reaction and N-Heteroannulation

Contributor(s): Victor Snieckus, Zhongdong Zhao
B. C. G. Soderberg*, J. W. Hubbard, S. R. Rector, S. N. O’Neil
West Virginia University, Morgantown, USA
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21. September 2005 (online)


A new synthetic route to 3,4-fused indoles by two Pd-catalyzed reactions - intramolecular Heck and reductive N-heteroannulation - is reported. Indoles with various ring sizes (6-8) anchored to the 3- and 4- position of the indole nucleus may be prepared by this method. A number of functional groups (e.g., Me, Ph, Ac, CO2Me) tolerate the conditions of this route. Both hetero­atom (N, O) containing and carbocyclic rings may be anellated to the indole moiety with acceptable yields.