Synthesis of tryptamine derivatives via a direct, one-pot reductive alkylation of indoles.
An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile approach employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates several functional groups. The new procedure was efficiently applied to a gram-scale synthesis of both luzindole, a reference MT2-selective melatonin receptor antagonist, and melatonin.
Department of Biomolecular Sciences, University of Urbino, Piazza Rinascimento 6, 61029 Urbino (PU), Italy.
Marika
M
Righi
Francesca
F
Topi
Silvia
S
Bartolucci
Annalida
A
Bedini
Giovanni
G
Piersanti
Gilberto
G
Spadoni
D000478:Alkylation; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014363:Tryptamines / Q000138:chemical synthesis* / Q000737:chemistry
D007211:Indoles; D014363:Tryptamines; C030820:tryptamine