Synthesis Of 2-Acyltetrahydro-β-Carbolines By An Intramolecular α-Amidoalkylation Reaction

1 February 1999

journal article
research article
Published by Taylor & Francis in Synthetic Communications

Vol. 29 (3) , 487-494
https://doi.org/10.1080/00397919908085791

Abstract

2-Acyltetrahydro-β-carbolines 7 have been obtained by cyclization of adducts 5 from imines 3 of tryptamine 1 and aldehydes 2 with acyl chlorides 4 as a result of an intramolecular a-amidoalkylation reaction in the presence of bases as N,N-dimethylaniline or Et₃N.

Keywords

This publication has 9 references indexed in Scilit:

A New Evidence for the Presence of a Spiroindolenium Species in the Pictet-Spengler Reaction
HETEROCYCLES, 1992
New Modification of the Intramolecular α-Amidoalkylation for the Synthesis of 2-Acyl-1,2,3,4-tetrahydroisoquinolines
Synthesis, 1989
On the stereochemistry of the Pictet-Spengler reaction
Tetrahedron Letters, 1987
Pictet-Spengler reactions of Tryptamine and tryptophan with cycloalkanones and ketonicMannich bases
Monatshefte für Chemie / Chemical Monthly, 1985
Pictet-Spengler reactions in aprotic media
The Journal of Organic Chemistry, 1984
Some 3-Carboxamides of b-Carboline and Tetrahydro-b-carboline
HETEROCYCLES, 1984
Study of the Pictet-Spengler reaction in aprotic media: synthesis of the .beta.-galactosidase inhibitor, pyridindolol
The Journal of Organic Chemistry, 1979
The Synthesis of Indole Alkaloids
Published by Wiley ,1977
Reaktionen der 1-Aryl-1.2.3.4-tetrahydro-β-carboline in saurer Lösung
European Journal of Organic Chemistry, 1965