41645-07-2Relevant academic research and scientific papers
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.
Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation
Song, Hao,Yang, Jun,Chen, Wei,Qin, Yong
, p. 6011 - 6014 (2007/10/03)
(Chemical Equation Presented) A new and efficient synthetic route to chiral 3-substituted hexahydropyrroloindoline 18 possessing absolute configurations in accordance with indole alkaloids has been developed from readily available L-tryptophan. The key step relies on the one-pot cascade reaction of oxazolidinone 17 with diazoester, which proceeds through intermolecular cyclopropanation, ring opening, and cyclization.
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.
Inverse electron demand Diels-Alder reactions of indole V. Reactions of 3-substituted indoles with heteroaromatic azadienes
Benson, Scott C.,Lee, Lily,Snyder, John K.
, p. 5061 - 5064 (2007/10/03)
The inverse electron demand Diels-Alder reactions of 3-substituted indoles with 1,2,4-triazines and 1,2,4,5-tetrazines proceeded in excellent yields both inter- and intramolecularly. The cycloaddition of tryptophan with a tethered 1,2,4-triazine produced a diastereomerically pure cycloadduct.
