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Communication | Special issue | Vol 80, No. 2, 2010, pp.831-840
Published online, 10th September, 2009
DOI: 10.3987/COM-09-S(S)99
Nucleophilic Addition of Hetaryllithium Compounds to 3-Nitro-1-(phenylsulfonyl)indole: Synthesis of Tetracyclic Thieno[3,2-c]-δ-carbolines

Philip E. Alford, Tara L. S. Kishbaugh, and Gordon W. Gribble*

*Department of Chemistry, Dartmouth College, 6128 Burke Laboratory, Hanover,
New Hampshire 03755, U.S.A.

Abstract

3-Nitro-1-(phenylsulfonyl)indole undergoes addition of aryl- and hetaryllithium nucleophiles to produce 2-substituted-3-nitroindoles. Mild reductive–acylation provides excellent access to 3-amido-2-hetarylindoles from which new thieno[3,2-c]-δ-carbolines are synthesized by cyclodehydration.