Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence |
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| Authors: | Chauder Brian Larkin Andrew Snieckus Victor |
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| Institution: | Department of Chemistry, Queen's University, Kingston, ON, K7L 3N6, Canada. |
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| Abstract: | reaction: see text] In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced. |
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