40247-57-2Relevant articles and documents
Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.
Chauder, Brian,Larkin, Andrew,Snieckus, Victor
, p. 815 - 817 (2007/10/03)
[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.
DIRECTED LITHIATION OF 1-TRIISOPROPYLSILYLGRAMINE. A SHORT ACCESS TO 3,4-DISUBSTITUTED INDOLES
Iwao, Masatomo
, p. 29 - 32 (2007/10/02)
1-Triisopropylsilylgramine was lithiated regioselectively at C-4 by treatment with t-BuLi in ether at 0 deg C for 1 h.The lithiated species was trapped with a variety of electrophiles to furnish 4-functionalized gramine derivatives in good yields.Replacement of the triisopropylsilyl protecting group by a methyl group resulted in C-2 selective lithiation under the similar reaction conditions.