41645-07-2Relevant articles and documents
Synthesis of tryptamine derivatives via a direct, one-pot reductive alkylation of indoles
Righi, Marika,Topi, Francesca,Bartolucci, Silvia,Bedini, Annalida,Piersanti, Giovanni,Spadoni, Gilberto
experimental part, p. 6351 - 6357 (2012/10/08)
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.
Intramolecular inverse electron demand Diels-Alder reactions of tryptamine with tethered heteroaromatic azadienes
Benson, Scott C.,Lee, Lily,Yang, Lydie,Snyder, John K.
, p. 1165 - 1180 (2007/10/03)
1,2,4,5-Tetrazines and 1,2,4-triazines tethered to tryptamine via the ethylamine side chain undergo intramolecular inverse electron demand cycloadditions to produce adducts with the [ABazaCE]-ring skeleton of the Aspidosperma alkaloids. (C) 2000 Elsevier Science Ltd.