4560-07-0Relevant articles and documents
Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: Exploiting N-protected β-amino alcohols as alkylating agents
Bartolucci, Silvia,Mari, Michele,Bedini, Annalida,Piersanti, Giovanni,Spadoni, Gilberto
, p. 3217 - 3222 (2015/03/30)
The selective C3-alkylation of indoles with N-protected ethanolamines involving the "borrowing hydrogen" strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.
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.
Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines
Nenajdenko, Valentine G.,Zakurdaev, Eugene P.,Prusov, Eugene V.,Balenkova, Elizabeth S.
, p. 11719 - 11724 (2007/10/03)
A new method for the synthesis of 2- and 3-substituted indolylalkylamides, derivatives of melatonin, from arylhydrazines and amidoketones by the Fischer reaction was elaborated. The amidoketones can be easily prepared from cyclic imines by reaction with acylpyridinium chloride. This method is a one-step synchronous creation of the selected alkylamide fragment and the indole core. Variation of the arylhydrazines create the desired substituents in the carbocycle of indolylalkylamides and suitable choice of amidoketone can direct the amidoalkyl chain to the 2- or 3-position of the indole. Graphical Abstract
